diff --git a/.eslintrc.js b/.eslintrc.js
index edfcaa2cb72..026366245b9 100644
--- a/.eslintrc.js
+++ b/.eslintrc.js
@@ -180,6 +180,7 @@ module.exports = {
         'aws-toolkits/no-console-log': 'error',
         'aws-toolkits/no-json-stringify-in-log': 'error',
         'aws-toolkits/no-printf-mismatch': 'error',
+        'aws-toolkits/no-index-import': 'error',
         'no-restricted-imports': [
             'error',
             {
diff --git a/packages/core/src/amazonq/commons/connector/baseMessenger.ts b/packages/core/src/amazonq/commons/connector/baseMessenger.ts
index 4c29f005557..1401bf5ff42 100644
--- a/packages/core/src/amazonq/commons/connector/baseMessenger.ts
+++ b/packages/core/src/amazonq/commons/connector/baseMessenger.ts
@@ -5,7 +5,6 @@
 
 import { ChatItemAction, ProgressField } from '@aws/mynah-ui'
 import { AuthFollowUpType, AuthMessageDataMap } from '../../../amazonq/auth/model'
-import { FeatureAuthState } from '../../../codewhisperer'
 import { i18n } from '../../../shared/i18n-helper'
 import { CodeReference } from '../../../amazonq/webview/ui/connector'
 
@@ -28,6 +27,7 @@ import {
 import { FollowUpTypes } from '../types'
 import { messageWithConversationId } from '../../../amazonqFeatureDev/userFacingText'
 import { DeletedFileInfo, NewFileInfo } from '../../../amazonqFeatureDev/types'
+import { FeatureAuthState } from '../../../codewhisperer/util/authUtil'
 
 export class Messenger {
     public constructor(
diff --git a/packages/core/src/amazonq/commons/controllers/contentController.ts b/packages/core/src/amazonq/commons/controllers/contentController.ts
index 1380253f8eb..64e1254c21a 100644
--- a/packages/core/src/amazonq/commons/controllers/contentController.ts
+++ b/packages/core/src/amazonq/commons/controllers/contentController.ts
@@ -6,7 +6,7 @@
 import * as vscode from 'vscode'
 import path from 'path'
 import { Position, TextEditor, window } from 'vscode'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { amazonQDiffScheme, amazonQTabSuffix } from '../../../shared/constants'
 import { disposeOnEditorClose } from '../../../shared/utilities/editorUtilities'
 import {
@@ -15,7 +15,9 @@ import {
     getIndentedCode,
     getSelectionFromRange,
 } from '../../../shared/utilities/textDocumentUtilities'
-import { extractFileAndCodeSelectionFromMessage, fs, getErrorMsg, ToolkitError } from '../../../shared'
+import { ToolkitError, getErrorMsg } from '../../../shared/errors'
+import fs from '../../../shared/fs/fs'
+import { extractFileAndCodeSelectionFromMessage } from '../../../shared/utilities/textUtilities'
 import { UserWrittenCodeTracker } from '../../../codewhisperer/tracker/userWrittenCodeTracker'
 
 export class ContentProvider implements vscode.TextDocumentContentProvider {
diff --git a/packages/core/src/amazonq/commons/diff.ts b/packages/core/src/amazonq/commons/diff.ts
index aac25d236d8..566327b6d22 100644
--- a/packages/core/src/amazonq/commons/diff.ts
+++ b/packages/core/src/amazonq/commons/diff.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { fs } from '../../shared'
+import { fs } from '../../shared/fs/fs'
 import { diffLines } from 'diff'
 
 export async function openDiff(leftPath: string, rightPath: string, tabId: string, scheme: string) {
diff --git a/packages/core/src/amazonq/commons/session/sessionConfigFactory.ts b/packages/core/src/amazonq/commons/session/sessionConfigFactory.ts
index d6dff48fbe5..0bc4a30c14a 100644
--- a/packages/core/src/amazonq/commons/session/sessionConfigFactory.ts
+++ b/packages/core/src/amazonq/commons/session/sessionConfigFactory.ts
@@ -5,8 +5,9 @@
 
 import * as vscode from 'vscode'
 import { WorkspaceFolderNotFoundError } from '../../../amazonqFeatureDev/errors'
-import { VirtualFileSystem, VirtualMemoryFile } from '../../../shared'
 import { CurrentWsFolders } from '../../../amazonqFeatureDev/types'
+import { VirtualFileSystem } from '../../../shared/virtualFilesystem'
+import { VirtualMemoryFile } from '../../../shared/virtualMemoryFile'
 
 export interface SessionConfig {
     // The paths on disk to where the source code lives
diff --git a/packages/core/src/amazonq/explorer/amazonQChildrenNodes.ts b/packages/core/src/amazonq/explorer/amazonQChildrenNodes.ts
index 7dfb7b33820..86648b41361 100644
--- a/packages/core/src/amazonq/explorer/amazonQChildrenNodes.ts
+++ b/packages/core/src/amazonq/explorer/amazonQChildrenNodes.ts
@@ -11,8 +11,10 @@ import { installAmazonQExtension } from '../../codewhisperer/commands/basicComma
 import { amazonQHelpUrl } from '../../shared/constants'
 import { cwTreeNodeSource } from '../../codewhisperer/commands/types'
 import { VSCODE_EXTENSION_ID } from '../../shared/extensions'
-import { globals, setContext } from '../../shared'
-import { ExtStartUpSources, telemetry } from '../../shared/telemetry'
+import globals from '../../shared/extensionGlobals'
+import { setContext } from '../../shared/vscode/setContext'
+import { telemetry } from '../../shared/telemetry/telemetry'
+import { ExtStartUpSources } from '../../shared/telemetry/util'
 import { ExtensionUse } from '../../auth/utils'
 
 const localize = nls.loadMessageBundle()
diff --git a/packages/core/src/amazonq/extApi.ts b/packages/core/src/amazonq/extApi.ts
index 874ee018526..2eb16e4cde2 100644
--- a/packages/core/src/amazonq/extApi.ts
+++ b/packages/core/src/amazonq/extApi.ts
@@ -4,11 +4,11 @@
  */
 
 import vscode from 'vscode'
-import { VSCODE_EXTENSION_ID } from '../shared/utilities'
+import { VSCODE_EXTENSION_ID } from '../shared/extensions'
 import { SendMessageCommandOutput, SendMessageRequest } from '@amzn/amazon-q-developer-streaming-client'
 import { GenerateAssistantResponseCommandOutput, GenerateAssistantResponseRequest } from '@amzn/codewhisperer-streaming'
 import { FeatureAuthState } from '../codewhisperer/util/authUtil'
-import { ToolkitError } from '../shared'
+import { ToolkitError } from '../shared/errors'
 
 /**
  * This interface is used and exported by the amazon q extension. If you make a change here then
diff --git a/packages/core/src/amazonq/index.ts b/packages/core/src/amazonq/index.ts
index 9ca9af7687c..b42a0c20a39 100644
--- a/packages/core/src/amazonq/index.ts
+++ b/packages/core/src/amazonq/index.ts
@@ -43,7 +43,7 @@ export { ExtensionMessage } from '../amazonq/webview/ui/commands'
 export { CodeReference } from '../codewhispererChat/view/connector/connector'
 export { extractAuthFollowUp } from './util/authUtils'
 export { Messenger } from './commons/connector/baseMessenger'
-import { FeatureContext } from '../shared'
+import { FeatureContext } from '../shared/featureConfig'
 
 /**
  * main from createMynahUI is a purely browser dependency. Due to this
diff --git a/packages/core/src/amazonq/lsp/lspClient.ts b/packages/core/src/amazonq/lsp/lspClient.ts
index 3969a3313e9..b5b506818d8 100644
--- a/packages/core/src/amazonq/lsp/lspClient.ts
+++ b/packages/core/src/amazonq/lsp/lspClient.ts
@@ -32,7 +32,9 @@ import {
 } from './types'
 import { Writable } from 'stream'
 import { CodeWhispererSettings } from '../../codewhisperer/util/codewhispererSettings'
-import { fs, getLogger, globals } from '../../shared'
+import { fs } from '../../shared/fs/fs'
+import { getLogger } from '../../shared/logger/logger'
+import globals from '../../shared/extensionGlobals'
 
 const localize = nls.loadMessageBundle()
 
diff --git a/packages/core/src/amazonq/lsp/lspController.ts b/packages/core/src/amazonq/lsp/lspController.ts
index b166b7c0b09..37afed70db0 100644
--- a/packages/core/src/amazonq/lsp/lspController.ts
+++ b/packages/core/src/amazonq/lsp/lspController.ts
@@ -16,9 +16,11 @@ import AdmZip from 'adm-zip'
 import { RelevantTextDocument } from '@amzn/codewhisperer-streaming'
 import { makeTemporaryToolkitFolder, tryRemoveFolder } from '../../shared/filesystemUtilities'
 import { activate as activateLsp } from './lspClient'
-import { telemetry } from '../../shared/telemetry'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { isCloud9 } from '../../shared/extensionUtilities'
-import { fs, globals, ToolkitError } from '../../shared'
+import { fs } from '../../shared/fs/fs'
+import globals from '../../shared/extensionGlobals'
+import { ToolkitError } from '../../shared/errors'
 import { isWeb } from '../../shared/extensionGlobals'
 import { getUserAgent } from '../../shared/telemetry/util'
 import { isAmazonInternalOs } from '../../shared/vscode/env'
diff --git a/packages/core/src/amazonq/messages/chatMessageDuration.ts b/packages/core/src/amazonq/messages/chatMessageDuration.ts
index d4b087f64df..6321489da62 100644
--- a/packages/core/src/amazonq/messages/chatMessageDuration.ts
+++ b/packages/core/src/amazonq/messages/chatMessageDuration.ts
@@ -4,8 +4,8 @@
  */
 
 import AsyncLock from 'async-lock'
-import { globals } from '../../shared'
-import { telemetry } from '../../shared/telemetry'
+import globals from '../../shared/extensionGlobals'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { Event, uiEventRecorder } from '../util/eventRecorder'
 import { CWCTelemetryHelper } from '../../codewhispererChat/controllers/chat/telemetryHelper'
 import { TabType } from '../webview/ui/storages/tabsStorage'
diff --git a/packages/core/src/amazonq/onboardingPage/walkthrough.ts b/packages/core/src/amazonq/onboardingPage/walkthrough.ts
index 466b6970b91..cb56c8b2abb 100644
--- a/packages/core/src/amazonq/onboardingPage/walkthrough.ts
+++ b/packages/core/src/amazonq/onboardingPage/walkthrough.ts
@@ -6,7 +6,7 @@
 import { focusAmazonQPanel } from '../../codewhispererChat/commands/registerCommands'
 import globals, { isWeb } from '../../shared/extensionGlobals'
 import { VSCODE_EXTENSION_ID } from '../../shared/extensions'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { localize } from '../../shared/utilities/vsCodeUtils'
 import { Commands, placeholder } from '../../shared/vscode/commands2'
 import vscode from 'vscode'
diff --git a/packages/core/src/amazonq/util/authUtils.ts b/packages/core/src/amazonq/util/authUtils.ts
index 0fd48ebc4c9..e310dbe9823 100644
--- a/packages/core/src/amazonq/util/authUtils.ts
+++ b/packages/core/src/amazonq/util/authUtils.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { FeatureAuthState } from '../../codewhisperer'
+import { FeatureAuthState } from '../../codewhisperer/util/authUtil'
 import { AuthFollowUpType, AuthMessageDataMap } from '../auth/model'
 
 /**
diff --git a/packages/core/src/amazonq/webview/generators/webViewContent.ts b/packages/core/src/amazonq/webview/generators/webViewContent.ts
index ea577574d4c..81c6cb00a35 100644
--- a/packages/core/src/amazonq/webview/generators/webViewContent.ts
+++ b/packages/core/src/amazonq/webview/generators/webViewContent.ts
@@ -6,7 +6,9 @@
 import path from 'path'
 import { Uri, Webview } from 'vscode'
 import { AuthUtil } from '../../../codewhisperer/util/authUtil'
-import { FeatureConfigProvider, FeatureContext, globals, isSageMaker } from '../../../shared'
+import { FeatureConfigProvider, FeatureContext } from '../../../shared/featureConfig'
+import globals from '../../../shared/extensionGlobals'
+import { isSageMaker } from '../../../shared/extensionUtilities'
 
 export class WebViewContentGenerator {
     private async generateFeatureConfigsData(): Promise<string> {
diff --git a/packages/core/src/amazonq/webview/messages/messageDispatcher.ts b/packages/core/src/amazonq/webview/messages/messageDispatcher.ts
index fdd1584b767..483b4525298 100644
--- a/packages/core/src/amazonq/webview/messages/messageDispatcher.ts
+++ b/packages/core/src/amazonq/webview/messages/messageDispatcher.ts
@@ -7,12 +7,13 @@ import { Webview, Uri } from 'vscode'
 import { MessagePublisher } from '../../messages/messagePublisher'
 import { MessageListener } from '../../messages/messageListener'
 import { TabType } from '../ui/storages/tabsStorage'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { amazonqMark } from '../../../shared/performance/marks'
-import { telemetry } from '../../../shared/telemetry'
+import { telemetry } from '../../../shared/telemetry/telemetry'
 import { AmazonQChatMessageDuration } from '../../messages/chatMessageDuration'
-import { globals, openUrl } from '../../../shared'
 import { isClickTelemetry, isOpenAgentTelemetry } from '../ui/telemetry/actions'
+import globals from '../../../shared/extensionGlobals'
+import { openUrl } from '../../../shared/utilities/vsCodeUtils'
 import { DefaultAmazonQAppInitContext } from '../../apps/initContext'
 
 export function dispatchWebViewMessagesToApps(
diff --git a/packages/core/src/amazonq/webview/ui/main.ts b/packages/core/src/amazonq/webview/ui/main.ts
index 74ada92cc67..1c940c6bea1 100644
--- a/packages/core/src/amazonq/webview/ui/main.ts
+++ b/packages/core/src/amazonq/webview/ui/main.ts
@@ -26,7 +26,7 @@ import { TextMessageHandler } from './messages/handler'
 import { MessageController } from './messages/controller'
 import { getActions, getDetails } from './diffTree/actions'
 import { DiffTreeFileInfo } from './diffTree/types'
-import { FeatureContext } from '../../../shared'
+import { FeatureContext } from '../../../shared/featureConfig'
 import { tryNewMap } from '../../util/functionUtils'
 import { welcomeScreenTabData } from './walkthrough/welcome'
 import { agentWalkthroughDataModel } from './walkthrough/agent'
diff --git a/packages/core/src/amazonq/webview/ui/tabs/generator.ts b/packages/core/src/amazonq/webview/ui/tabs/generator.ts
index a6d31e715df..f037e4c56ef 100644
--- a/packages/core/src/amazonq/webview/ui/tabs/generator.ts
+++ b/packages/core/src/amazonq/webview/ui/tabs/generator.ts
@@ -9,7 +9,7 @@ import { FollowUpGenerator } from '../followUps/generator'
 import { QuickActionGenerator } from '../quickActions/generator'
 import { TabTypeDataMap } from './constants'
 import { agentWalkthroughDataModel } from '../walkthrough/agent'
-import { FeatureContext } from '../../../../shared'
+import { FeatureContext } from '../../../../shared/featureConfig'
 
 export interface TabDataGeneratorProps {
     isFeatureDevEnabled: boolean
diff --git a/packages/core/src/amazonqDoc/app.ts b/packages/core/src/amazonqDoc/app.ts
index 1847da2e168..bf64c71c387 100644
--- a/packages/core/src/amazonqDoc/app.ts
+++ b/packages/core/src/amazonqDoc/app.ts
@@ -9,7 +9,7 @@ import { AmazonQAppInitContext } from '../amazonq/apps/initContext'
 import { MessagePublisher } from '../amazonq/messages/messagePublisher'
 import { MessageListener } from '../amazonq/messages/messageListener'
 import { fromQueryToParameters } from '../shared/utilities/uriUtils'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { AuthUtil } from '../codewhisperer/util/authUtil'
 import { debounce } from 'lodash'
 import { DocChatSessionStorage } from './storages/chatSession'
diff --git a/packages/core/src/amazonqDoc/controllers/chat/controller.ts b/packages/core/src/amazonqDoc/controllers/chat/controller.ts
index 2f31346d9cd..7b48f1b361e 100644
--- a/packages/core/src/amazonqDoc/controllers/chat/controller.ts
+++ b/packages/core/src/amazonqDoc/controllers/chat/controller.ts
@@ -18,7 +18,7 @@ import {
     findReadmePath,
 } from '../../constants'
 import { AuthUtil } from '../../../codewhisperer/util/authUtil'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 
 import { Session } from '../../session/session'
 import { i18n } from '../../../shared/i18n-helper'
diff --git a/packages/core/src/amazonqDoc/controllers/docGenerationTask.ts b/packages/core/src/amazonqDoc/controllers/docGenerationTask.ts
index be345884fd2..8b854037282 100644
--- a/packages/core/src/amazonqDoc/controllers/docGenerationTask.ts
+++ b/packages/core/src/amazonqDoc/controllers/docGenerationTask.ts
@@ -9,7 +9,7 @@ import {
     DocV2AcceptanceEvent,
     DocV2GenerationEvent,
 } from '../../codewhisperer/client/codewhispereruserclient'
-import { getLogger } from '../../shared'
+import { getLogger } from '../../shared/logger/logger'
 
 export class DocGenerationTask {
     // Telemetry fields
diff --git a/packages/core/src/amazonqDoc/messenger.ts b/packages/core/src/amazonqDoc/messenger.ts
index f28e5e9060b..3c6abfdf15f 100644
--- a/packages/core/src/amazonqDoc/messenger.ts
+++ b/packages/core/src/amazonqDoc/messenger.ts
@@ -4,7 +4,7 @@
  */
 import { Messenger } from '../amazonq/commons/connector/baseMessenger'
 import { AppToWebViewMessageDispatcher } from '../amazonq/commons/connector/connectorMessages'
-import { messageWithConversationId } from '../amazonqFeatureDev'
+import { messageWithConversationId } from '../amazonqFeatureDev/userFacingText'
 import { i18n } from '../shared/i18n-helper'
 import { docGenerationProgressMessage, DocGenerationStep, Mode, NewSessionFollowUps } from './constants'
 import { inProgress } from './types'
diff --git a/packages/core/src/amazonqDoc/session/session.ts b/packages/core/src/amazonqDoc/session/session.ts
index 4396e6e5e6b..f05bd98f661 100644
--- a/packages/core/src/amazonqDoc/session/session.ts
+++ b/packages/core/src/amazonqDoc/session/session.ts
@@ -7,10 +7,8 @@ import { docScheme, featureName, Mode } from '../constants'
 import { DeletedFileInfo, Interaction, NewFileInfo, SessionState, SessionStateConfig } from '../types'
 import { PrepareCodeGenState } from './sessionState'
 import { telemetry } from '../../shared/telemetry/telemetry'
-import { extensionVersion, fs, getLogger, globals } from '../../shared'
 import { AuthUtil } from '../../codewhisperer/util/authUtil'
 import { SessionConfig } from '../../amazonq/commons/session/sessionConfigFactory'
-import { ReferenceLogViewProvider } from '../../codewhisperer'
 import path from 'path'
 import { FeatureDevClient } from '../../amazonqFeatureDev/client/featureDev'
 import { TelemetryHelper } from '../../amazonqFeatureDev/util/telemetryHelper'
@@ -27,6 +25,11 @@ import {
 import { getClientId, getOperatingSystem, getOptOutPreference } from '../../shared/telemetry/util'
 import { DocMessenger } from '../messenger'
 import { computeDiff } from '../../amazonq/commons/diff'
+import { ReferenceLogViewProvider } from '../../codewhisperer/service/referenceLogViewProvider'
+import fs from '../../shared/fs/fs'
+import globals from '../../shared/extensionGlobals'
+import { extensionVersion } from '../../shared/vscode/env'
+import { getLogger } from '../../shared/logger/logger'
 
 export class Session {
     private _state?: SessionState | Omit<SessionState, 'uploadId'>
diff --git a/packages/core/src/amazonqDoc/session/sessionState.ts b/packages/core/src/amazonqDoc/session/sessionState.ts
index 7bf9c02e51b..d1a38b3f3e0 100644
--- a/packages/core/src/amazonqDoc/session/sessionState.ts
+++ b/packages/core/src/amazonqDoc/session/sessionState.ts
@@ -6,7 +6,7 @@
 import * as vscode from 'vscode'
 import { ToolkitError } from '../../shared/errors'
 import globals from '../../shared/extensionGlobals'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { telemetry } from '../../shared/telemetry/telemetry'
 import { VirtualFileSystem } from '../../shared/virtualFilesystem'
 import { DocGenerationStep, docScheme, getFileSummaryPercentage, Mode } from '../constants'
@@ -28,14 +28,10 @@ import {
     SessionStateInteraction,
     SessionStatePhase,
 } from '../types'
-import {
-    EmptyCodeGenID,
-    Intent,
-    TelemetryHelper,
-    getDeletedFileInfos,
-    prepareRepoData,
-    registerNewFiles,
-} from '../../amazonqFeatureDev'
+import { TelemetryHelper } from '../../amazonqFeatureDev/util/telemetryHelper'
+import { EmptyCodeGenID, getDeletedFileInfos, registerNewFiles } from '../../amazonqFeatureDev/session/sessionState'
+import { Intent } from '../../amazonqFeatureDev/types'
+import { prepareRepoData } from '../../amazonqFeatureDev/util/files'
 import { uploadCode } from '../../amazonqFeatureDev/util/upload'
 import {
     ContentLengthError,
diff --git a/packages/core/src/amazonqFeatureDev/app.ts b/packages/core/src/amazonqFeatureDev/app.ts
index a72851e8ac7..0af05cf0530 100644
--- a/packages/core/src/amazonqFeatureDev/app.ts
+++ b/packages/core/src/amazonqFeatureDev/app.ts
@@ -10,7 +10,7 @@ import { AmazonQAppInitContext } from '../amazonq/apps/initContext'
 import { MessagePublisher } from '../amazonq/messages/messagePublisher'
 import { MessageListener } from '../amazonq/messages/messageListener'
 import { fromQueryToParameters } from '../shared/utilities/uriUtils'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { TabIdNotFoundError } from './errors'
 import { featureDevChat, featureDevScheme } from './constants'
 import globals from '../shared/extensionGlobals'
diff --git a/packages/core/src/amazonqFeatureDev/client/featureDev.ts b/packages/core/src/amazonqFeatureDev/client/featureDev.ts
index 01be84828b3..0017045cdfb 100644
--- a/packages/core/src/amazonqFeatureDev/client/featureDev.ts
+++ b/packages/core/src/amazonqFeatureDev/client/featureDev.ts
@@ -8,7 +8,7 @@ import { omit } from 'lodash'
 import { AuthUtil } from '../../codewhisperer/util/authUtil'
 import { ServiceOptions } from '../../shared/awsClientBuilder'
 import globals from '../../shared/extensionGlobals'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import * as FeatureDevProxyClient from './featuredevproxyclient'
 import { featureName } from '../constants'
 import { CodeReference } from '../../amazonq/webview/ui/connector'
@@ -25,7 +25,7 @@ import { createCodeWhispererChatStreamingClient } from '../../shared/clients/cod
 import { getClientId, getOptOutPreference, getOperatingSystem } from '../../shared/telemetry/util'
 import { extensionVersion } from '../../shared/vscode/env'
 import apiConfig = require('./codewhispererruntime-2022-11-11.json')
-import { UserWrittenCodeTracker } from '../../codewhisperer'
+import { UserWrittenCodeTracker } from '../../codewhisperer/tracker/userWrittenCodeTracker'
 import {
     FeatureDevCodeAcceptanceEvent,
     FeatureDevCodeGenerationEvent,
diff --git a/packages/core/src/amazonqFeatureDev/controllers/chat/controller.ts b/packages/core/src/amazonqFeatureDev/controllers/chat/controller.ts
index 6ce82a1a0ab..0fbd94eb47d 100644
--- a/packages/core/src/amazonqFeatureDev/controllers/chat/controller.ts
+++ b/packages/core/src/amazonqFeatureDev/controllers/chat/controller.ts
@@ -33,7 +33,7 @@ import { featureDevScheme, featureName, generateDevFilePrompt } from '../../cons
 import { DeletedFileInfo, DevPhase, MetricDataOperationName, MetricDataResult, type NewFileInfo } from '../../types'
 import { AuthUtil } from '../../../codewhisperer/util/authUtil'
 import { AuthController } from '../../../amazonq/auth/controller'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { submitFeedback } from '../../../feedback/vue/submitFeedback'
 import { placeholder } from '../../../shared/vscode/commands2'
 import { EditorContentController } from '../../../amazonq/commons/controllers/contentController'
@@ -44,8 +44,8 @@ import { getWorkspaceFoldersByPrefixes } from '../../../shared/utilities/workspa
 import { openDeletedDiff, openDiff } from '../../../amazonq/commons/diff'
 import { i18n } from '../../../shared/i18n-helper'
 import globals from '../../../shared/extensionGlobals'
-import { CodeWhispererSettings } from '../../../codewhisperer'
-import { randomUUID } from '../../../shared'
+import { CodeWhispererSettings } from '../../../codewhisperer/util/codewhispererSettings'
+import { randomUUID } from '../../../shared/crypto'
 import { FollowUpTypes } from '../../../amazonq/commons/types'
 import { Messenger } from '../../../amazonq/commons/connector/baseMessenger'
 import { BaseChatSessionStorage } from '../../../amazonq/commons/baseChatStorage'
diff --git a/packages/core/src/amazonqFeatureDev/session/session.ts b/packages/core/src/amazonqFeatureDev/session/session.ts
index a1de23d1861..55f3f4cba58 100644
--- a/packages/core/src/amazonqFeatureDev/session/session.ts
+++ b/packages/core/src/amazonqFeatureDev/session/session.ts
@@ -23,7 +23,7 @@ import { telemetry } from '../../shared/telemetry/telemetry'
 import { TelemetryHelper } from '../util/telemetryHelper'
 import { ReferenceLogViewProvider } from '../../codewhisperer/service/referenceLogViewProvider'
 import { AuthUtil } from '../../codewhisperer/util/authUtil'
-import { getLogger } from '../../shared'
+import { getLogger } from '../../shared/logger/logger'
 import { logWithConversationId } from '../userFacingText'
 import { CodeReference } from '../../amazonq/webview/ui/connector'
 import { MynahIcons } from '@aws/mynah-ui'
diff --git a/packages/core/src/amazonqFeatureDev/session/sessionState.ts b/packages/core/src/amazonqFeatureDev/session/sessionState.ts
index f3cd49eb972..85d125a8647 100644
--- a/packages/core/src/amazonqFeatureDev/session/sessionState.ts
+++ b/packages/core/src/amazonqFeatureDev/session/sessionState.ts
@@ -8,7 +8,7 @@ import * as path from 'path'
 import * as vscode from 'vscode'
 import { ToolkitError } from '../../shared/errors'
 import globals from '../../shared/extensionGlobals'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { telemetry } from '../../shared/telemetry/telemetry'
 import { VirtualFileSystem } from '../../shared/virtualFilesystem'
 import { VirtualMemoryFile } from '../../shared/virtualMemoryFile'
diff --git a/packages/core/src/amazonqFeatureDev/util/files.ts b/packages/core/src/amazonqFeatureDev/util/files.ts
index b0949edeca1..3c0b240657d 100644
--- a/packages/core/src/amazonqFeatureDev/util/files.ts
+++ b/packages/core/src/amazonqFeatureDev/util/files.ts
@@ -16,8 +16,8 @@ import { AmazonqCreateUpload, Span, telemetry as amznTelemetry } from '../../sha
 import { TelemetryHelper } from './telemetryHelper'
 import { maxRepoSizeBytes } from '../constants'
 import { isCodeFile } from '../../shared/filetypes'
-import { fs } from '../../shared'
-import { CodeWhispererSettings } from '../../codewhisperer'
+import { fs } from '../../shared/fs/fs'
+import { CodeWhispererSettings } from '../../codewhisperer/util/codewhispererSettings'
 import { ZipStream } from '../../shared/utilities/zipStream'
 
 export async function checkForDevFile(root: string) {
diff --git a/packages/core/src/amazonqFeatureDev/util/telemetryHelper.ts b/packages/core/src/amazonqFeatureDev/util/telemetryHelper.ts
index 111dd19f17e..8272d9ec7e5 100644
--- a/packages/core/src/amazonqFeatureDev/util/telemetryHelper.ts
+++ b/packages/core/src/amazonqFeatureDev/util/telemetryHelper.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { globals } from '../../shared'
+import globals from '../../shared/extensionGlobals'
 import { getLogger } from '../../shared/logger/logger'
 import { AmazonqApproachInvoke, AmazonqCodeGenerationInvoke, Span } from '../../shared/telemetry/telemetry'
 import { LLMResponseType } from '../types'
diff --git a/packages/core/src/amazonqFeatureDev/util/upload.ts b/packages/core/src/amazonqFeatureDev/util/upload.ts
index f9324cfacb8..43312ba9c35 100644
--- a/packages/core/src/amazonqFeatureDev/util/upload.ts
+++ b/packages/core/src/amazonqFeatureDev/util/upload.ts
@@ -8,7 +8,7 @@ import { getLogger } from '../../shared/logger/logger'
 import { featureName } from '../constants'
 
 import { UploadCodeError, UploadURLExpired } from '../errors'
-import { ToolkitError } from '../../shared'
+import { ToolkitError } from '../../shared/errors'
 import { i18n } from '../../shared/i18n-helper'
 
 /**
diff --git a/packages/core/src/amazonqGumby/activation.ts b/packages/core/src/amazonqGumby/activation.ts
index 87297bff1c6..74823f6fbc6 100644
--- a/packages/core/src/amazonqGumby/activation.ts
+++ b/packages/core/src/amazonqGumby/activation.ts
@@ -16,7 +16,7 @@ import { transformByQState } from '../codewhisperer/models/model'
 import { ProposedTransformationExplorer } from '../codewhisperer/service/transformByQ/transformationResultsViewProvider'
 import { CodeTransformTelemetryState } from './telemetry/codeTransformTelemetryState'
 import { telemetry } from '../shared/telemetry/telemetry'
-import { setContext } from '../shared'
+import { setContext } from '../shared/vscode/setContext'
 
 export async function activate(context: ExtContext) {
     void setContext('gumby.wasQCodeTransformationUsed', false)
diff --git a/packages/core/src/amazonqGumby/chat/controller/controller.ts b/packages/core/src/amazonqGumby/chat/controller/controller.ts
index 8fb73fbd4fc..efad8e5c970 100644
--- a/packages/core/src/amazonqGumby/chat/controller/controller.ts
+++ b/packages/core/src/amazonqGumby/chat/controller/controller.ts
@@ -12,7 +12,7 @@ import { GumbyNamedMessages, Messenger } from './messenger/messenger'
 import { AuthController } from '../../../amazonq/auth/controller'
 import { ChatSessionManager } from '../storages/chatSession'
 import { ConversationState, Session } from '../session/session'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { featureName } from '../../models/constants'
 import { AuthUtil } from '../../../codewhisperer/util/authUtil'
 import {
diff --git a/packages/core/src/amazonqGumby/telemetry/codeTransformMetadata.ts b/packages/core/src/amazonqGumby/telemetry/codeTransformMetadata.ts
index 219ee28e76c..22271a3b96b 100644
--- a/packages/core/src/amazonqGumby/telemetry/codeTransformMetadata.ts
+++ b/packages/core/src/amazonqGumby/telemetry/codeTransformMetadata.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 
 export const codeTransformMaxMetaDataLength = 65536
 
diff --git a/packages/core/src/amazonqScan/chat/storages/chatSession.ts b/packages/core/src/amazonqScan/chat/storages/chatSession.ts
index b9742a5db95..4feaca17675 100644
--- a/packages/core/src/amazonqScan/chat/storages/chatSession.ts
+++ b/packages/core/src/amazonqScan/chat/storages/chatSession.ts
@@ -4,7 +4,7 @@
  *
  */
 
-import { getLogger } from '../../../shared'
+import { getLogger } from '../../../shared/logger/logger'
 import { Session } from '../session/session'
 
 export class SessionNotFoundError extends Error {}
diff --git a/packages/core/src/amazonqTest/chat/controller/controller.ts b/packages/core/src/amazonqTest/chat/controller/controller.ts
index 2f3a0065838..4467f7fcb24 100644
--- a/packages/core/src/amazonqTest/chat/controller/controller.ts
+++ b/packages/core/src/amazonqTest/chat/controller/controller.ts
@@ -12,29 +12,6 @@ import { AuthController } from '../../../amazonq/auth/controller'
 import { ChatSessionManager } from '../storages/chatSession'
 import { BuildStatus, ConversationState, Session } from '../session/session'
 import { AuthUtil } from '../../../codewhisperer/util/authUtil'
-import {
-    CodeWhispererConstants,
-    ReferenceLogViewProvider,
-    ShortAnswer,
-    ShortAnswerReference,
-    TelemetryHelper,
-    TestGenerationBuildStep,
-    testGenState,
-    tooManyRequestErrorMessage,
-    unitTestGenerationCancelMessage,
-    UserWrittenCodeTracker,
-} from '../../../codewhisperer'
-import {
-    fs,
-    getLogger,
-    getTelemetryReasonDesc,
-    i18n,
-    openUrl,
-    randomUUID,
-    sleep,
-    tempDirPath,
-    testGenerationLogsDir,
-} from '../../../shared'
 import {
     buildProgressField,
     cancellingProgressField,
@@ -46,7 +23,7 @@ import {
     testGenSummaryMessage,
 } from '../../models/constants'
 import MessengerUtils, { ButtonActions } from './messenger/messengerUtils'
-import { isAwsError } from '../../../shared/errors'
+import { getTelemetryReasonDesc, isAwsError } from '../../../shared/errors'
 import { ChatItemType } from '../../../amazonq/commons/model'
 import { ProgressField } from '@aws/mynah-ui'
 import { FollowUpTypes } from '../../../amazonq/commons/types'
@@ -64,8 +41,26 @@ import { EditorContentController } from '../../../amazonq/commons/controllers/co
 import { amazonQTabSuffix } from '../../../shared/constants'
 import { applyChanges } from '../../../shared/utilities/textDocumentUtilities'
 import { telemetry } from '../../../shared/telemetry/telemetry'
-import { CodeReference } from '../../../amazonq'
 import { CodeWhispererSettings } from '../../../codewhisperer/util/codewhispererSettings'
+import { openUrl } from '../../../shared/utilities/vsCodeUtils'
+import { getLogger } from '../../../shared/logger/logger'
+import { i18n } from '../../../shared/i18n-helper'
+import { sleep } from '../../../shared/utilities/timeoutUtils'
+import { fs } from '../../../shared/fs/fs'
+import { randomUUID } from '../../../shared/crypto'
+import { tempDirPath, testGenerationLogsDir } from '../../../shared/filesystemUtilities'
+import { CodeReference } from '../../../codewhispererChat/view/connector/connector'
+import { TelemetryHelper } from '../../../codewhisperer/util/telemetryHelper'
+import { ShortAnswer, ShortAnswerReference, testGenState } from '../../../codewhisperer/models/model'
+import {
+    referenceLogText,
+    TestGenerationBuildStep,
+    tooManyRequestErrorMessage,
+    unitTestGenerationCancelMessage,
+    utgLimitReached,
+} from '../../../codewhisperer/models/constants'
+import { UserWrittenCodeTracker } from '../../../codewhisperer/tracker/userWrittenCodeTracker'
+import { ReferenceLogViewProvider } from '../../../codewhisperer/service/referenceLogViewProvider'
 
 export interface TestChatControllerEventEmitters {
     readonly tabOpened: vscode.EventEmitter<any>
@@ -281,7 +276,7 @@ export class TestController {
 
         // If user reached monthly limit for builderId
         if (error.code === 'CreateTestJobError') {
-            if (error.message.includes(CodeWhispererConstants.utgLimitReached)) {
+            if (error.message.includes(utgLimitReached)) {
                 getLogger().error('Monthly quota reached for QSDA actions.')
                 return this.messenger.sendMessage(
                     i18n('AWS.amazonq.featureDev.error.monthlyLimitReached'),
@@ -713,7 +708,7 @@ export class TestController {
             getLogger().debug('Extracted code slice: %s', code)
             const referenceLog =
                 `[${time}] Accepted recommendation ` +
-                CodeWhispererConstants.referenceLogText(
+                referenceLogText(
                     `<br><code>${code}</code><br>`,
                     reference.licenseName!,
                     reference.repository!,
diff --git a/packages/core/src/amazonqTest/chat/controller/messenger/messenger.ts b/packages/core/src/amazonqTest/chat/controller/messenger/messenger.ts
index f842a6c1808..b89be5c7144 100644
--- a/packages/core/src/amazonqTest/chat/controller/messenger/messenger.ts
+++ b/packages/core/src/amazonqTest/chat/controller/messenger/messenger.ts
@@ -36,8 +36,9 @@ import { CodeReference } from '../../../../amazonq/webview/ui/apps/amazonqCommon
 import { getHttpStatusCode, getRequestId, getTelemetryReasonDesc, ToolkitError } from '../../../../shared/errors'
 import { sleep, waitUntil } from '../../../../shared/utilities/timeoutUtils'
 import { keys } from '../../../../shared/utilities/tsUtils'
-import { TelemetryHelper, testGenState } from '../../../../codewhisperer'
 import { cancellingProgressField, testGenCompletedField } from '../../../models/constants'
+import { testGenState } from '../../../../codewhisperer/models/model'
+import { TelemetryHelper } from '../../../../codewhisperer/util/telemetryHelper'
 
 export type UnrecoverableErrorType = 'no-project-found' | 'no-open-file-found' | 'invalid-file-type'
 
diff --git a/packages/core/src/amazonqTest/chat/session/session.ts b/packages/core/src/amazonqTest/chat/session/session.ts
index 713b8fcf5f7..e6fb850a3fb 100644
--- a/packages/core/src/amazonqTest/chat/session/session.ts
+++ b/packages/core/src/amazonqTest/chat/session/session.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { ShortAnswer, ShortAnswerReference } from '../../../codewhisperer'
+import { ShortAnswer, ShortAnswerReference } from '../../../codewhisperer/models/model'
 import { TestGenerationJob } from '../../../codewhisperer/client/codewhispereruserclient'
 
 export enum ConversationState {
diff --git a/packages/core/src/amazonqTest/chat/storages/chatSession.ts b/packages/core/src/amazonqTest/chat/storages/chatSession.ts
index 99ef0a3b12e..a8a3ccf429d 100644
--- a/packages/core/src/amazonqTest/chat/storages/chatSession.ts
+++ b/packages/core/src/amazonqTest/chat/storages/chatSession.ts
@@ -5,7 +5,7 @@
  */
 
 import { Session } from '../session/session'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 
 export class SessionNotFoundError extends Error {}
 
diff --git a/packages/core/src/amazonqTest/models/constants.ts b/packages/core/src/amazonqTest/models/constants.ts
index 8370d4d3ca7..f836991643b 100644
--- a/packages/core/src/amazonqTest/models/constants.ts
+++ b/packages/core/src/amazonqTest/models/constants.ts
@@ -4,7 +4,7 @@
  */
 import { ProgressField, MynahIcons, ChatItemButton } from '@aws/mynah-ui'
 import { ButtonActions } from '../chat/controller/messenger/messengerUtils'
-import { TestGenerationBuildStep } from '../../codewhisperer'
+import { TestGenerationBuildStep } from '../../codewhisperer/models/constants'
 import { ChatSessionManager } from '../chat/storages/chatSession'
 import { BuildStatus } from '../chat/session/session'
 
diff --git a/packages/core/src/applicationcomposer/messageHandlers/emitTelemetryMessageHandler.ts b/packages/core/src/applicationcomposer/messageHandlers/emitTelemetryMessageHandler.ts
index 9b0506b9196..8210f126a42 100644
--- a/packages/core/src/applicationcomposer/messageHandlers/emitTelemetryMessageHandler.ts
+++ b/packages/core/src/applicationcomposer/messageHandlers/emitTelemetryMessageHandler.ts
@@ -20,7 +20,7 @@ import {
     AppcomposerInitializeProject,
     telemetry,
 } from '../../shared/telemetry/telemetry'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 
 export function emitTelemetryMessageHandler(message: EmitTelemetryMessage) {
     try {
diff --git a/packages/core/src/applicationcomposer/messageHandlers/logMessageHandler.ts b/packages/core/src/applicationcomposer/messageHandlers/logMessageHandler.ts
index 7753d6fbd9f..2565a2b8118 100644
--- a/packages/core/src/applicationcomposer/messageHandlers/logMessageHandler.ts
+++ b/packages/core/src/applicationcomposer/messageHandlers/logMessageHandler.ts
@@ -4,7 +4,7 @@
  */
 
 import { LogMessage } from '../types'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 
 export function logMessageHandler(message: LogMessage) {
     const logger = getLogger()
diff --git a/packages/core/src/applicationcomposer/webviewManager.ts b/packages/core/src/applicationcomposer/webviewManager.ts
index 8092a2c635f..884039f907b 100644
--- a/packages/core/src/applicationcomposer/webviewManager.ts
+++ b/packages/core/src/applicationcomposer/webviewManager.ts
@@ -7,7 +7,7 @@ import * as vscode from 'vscode'
 import * as nls from 'vscode-nls'
 import request from '../shared/request'
 import { ApplicationComposer } from './composerWebview'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 
 const localize = nls.loadMessageBundle()
 
diff --git a/packages/core/src/auth/activation.ts b/packages/core/src/auth/activation.ts
index 76c92cb7284..ce1e53e7ed4 100644
--- a/packages/core/src/auth/activation.ts
+++ b/packages/core/src/auth/activation.ts
@@ -7,7 +7,7 @@ import * as vscode from 'vscode'
 import { Auth } from './auth'
 import { LoginManager } from './deprecated/loginManager'
 import { fromString } from './providers/credentials'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { ExtensionUse, initializeCredentialsProviderManager } from './utils'
 import { isAmazonQ, isCloud9, isSageMaker } from '../shared/extensionUtilities'
 import { isInDevEnv } from '../shared/vscode/env'
diff --git a/packages/core/src/auth/auth.ts b/packages/core/src/auth/auth.ts
index fba0c80e261..000b5531334 100644
--- a/packages/core/src/auth/auth.ts
+++ b/packages/core/src/auth/auth.ts
@@ -18,7 +18,7 @@ import { getCache, getCacheFileWatcher } from './sso/cache'
 import { isNonNullable, Mutable } from '../shared/utilities/tsUtils'
 import { SsoToken, truncateStartUrl } from './sso/model'
 import { SsoClient } from './sso/clients'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { CredentialsProviderManager } from './providers/credentialsProviderManager'
 import { asString, CredentialsId, CredentialsProvider, fromString } from './providers/credentials'
 import { keyedDebounce, once } from '../shared/utilities/functionUtils'
diff --git a/packages/core/src/auth/credentials/sharedCredentialsFile.ts b/packages/core/src/auth/credentials/sharedCredentialsFile.ts
index 5d7ee7b727e..8760dce7b59 100644
--- a/packages/core/src/auth/credentials/sharedCredentialsFile.ts
+++ b/packages/core/src/auth/credentials/sharedCredentialsFile.ts
@@ -7,7 +7,7 @@
 
 import { join, resolve } from 'path'
 import fs from '../../shared/fs/fs'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 
 /**
  * Returns env var value if it is non-empty.
diff --git a/packages/core/src/auth/credentials/validation.ts b/packages/core/src/auth/credentials/validation.ts
index a82eb26a36a..70229e3786c 100644
--- a/packages/core/src/auth/credentials/validation.ts
+++ b/packages/core/src/auth/credentials/validation.ts
@@ -10,7 +10,7 @@ const localize = nls.loadMessageBundle()
 import { CredentialsData, CredentialsKey, SectionName, SharedCredentialsKeys } from './types'
 import { ToolkitError } from '../../shared/errors'
 import { profileExists } from './sharedCredentials'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 
 /** credentials keys and their associated error message, if they exists */
 type CredentialsErrors = CredentialsData
diff --git a/packages/core/src/auth/deprecated/loginManager.ts b/packages/core/src/auth/deprecated/loginManager.ts
index d60e735b740..b7c5a83d340 100644
--- a/packages/core/src/auth/deprecated/loginManager.ts
+++ b/packages/core/src/auth/deprecated/loginManager.ts
@@ -11,7 +11,7 @@ const localize = nls.loadMessageBundle()
 import * as vscode from 'vscode'
 import { CancellationError } from '../../shared/utilities/timeoutUtils'
 import { AwsContext } from '../../shared/awsContext'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { CredentialSourceId, CredentialType, Result } from '../../shared/telemetry/telemetry'
 import { CredentialsStore } from '../credentials/store'
 import { CredentialsSettings, showLoginFailedMessage } from '../credentials/utils'
diff --git a/packages/core/src/auth/providers/credentialsProviderManager.ts b/packages/core/src/auth/providers/credentialsProviderManager.ts
index a2736cabc18..f694640c6a1 100644
--- a/packages/core/src/auth/providers/credentialsProviderManager.ts
+++ b/packages/core/src/auth/providers/credentialsProviderManager.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { AwsLoadCredentials, telemetry } from '../../shared/telemetry/telemetry'
 import { withTelemetryContext } from '../../shared/telemetry/util'
 import { cancellableDebounce } from '../../shared/utilities/functionUtils'
diff --git a/packages/core/src/auth/providers/ec2CredentialsProvider.ts b/packages/core/src/auth/providers/ec2CredentialsProvider.ts
index ba8961f014a..773b2d3b564 100644
--- a/packages/core/src/auth/providers/ec2CredentialsProvider.ts
+++ b/packages/core/src/auth/providers/ec2CredentialsProvider.ts
@@ -7,7 +7,7 @@ import { Credentials } from '@aws-sdk/types'
 import { fromInstanceMetadata } from '@aws-sdk/credential-provider-imds'
 import { DefaultEc2MetadataClient } from '../../shared/clients/ec2MetadataClient'
 import { Ec2MetadataClient } from '../../shared/clients/ec2MetadataClient'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { CredentialType } from '../../shared/telemetry/telemetry.gen'
 import { getStringHash } from '../../shared/utilities/textUtilities'
 import { CredentialsId, CredentialsProvider, CredentialsProviderType } from './credentials'
diff --git a/packages/core/src/auth/providers/ecsCredentialsProvider.ts b/packages/core/src/auth/providers/ecsCredentialsProvider.ts
index c35d0232da4..10f09885166 100644
--- a/packages/core/src/auth/providers/ecsCredentialsProvider.ts
+++ b/packages/core/src/auth/providers/ecsCredentialsProvider.ts
@@ -9,7 +9,7 @@ import { EnvironmentVariables } from '../../shared/environmentVariables'
 import { CredentialType } from '../../shared/telemetry/telemetry.gen'
 import { getStringHash } from '../../shared/utilities/textUtilities'
 import { CredentialsId, CredentialsProvider, CredentialsProviderType } from './credentials'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import globals from '../../shared/extensionGlobals'
 
 /**
diff --git a/packages/core/src/auth/providers/sharedCredentialsProvider.ts b/packages/core/src/auth/providers/sharedCredentialsProvider.ts
index 561c346ad99..1693a6ed089 100644
--- a/packages/core/src/auth/providers/sharedCredentialsProvider.ts
+++ b/packages/core/src/auth/providers/sharedCredentialsProvider.ts
@@ -10,7 +10,7 @@ import { ParsedIniData, SharedConfigFiles } from '@smithy/shared-ini-file-loader
 import { chain } from '@aws-sdk/property-provider'
 import { fromInstanceMetadata, fromContainerMetadata } from '@aws-sdk/credential-provider-imds'
 import { fromEnv } from '@aws-sdk/credential-provider-env'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { getStringHash } from '../../shared/utilities/textUtilities'
 import { getMfaTokenFromUser, resolveProviderWithCancel } from '../credentials/utils'
 import { CredentialsProvider, CredentialsProviderType, CredentialsId } from './credentials'
diff --git a/packages/core/src/auth/providers/sharedCredentialsProviderFactory.ts b/packages/core/src/auth/providers/sharedCredentialsProviderFactory.ts
index 4864a332db0..93a0d96d475 100644
--- a/packages/core/src/auth/providers/sharedCredentialsProviderFactory.ts
+++ b/packages/core/src/auth/providers/sharedCredentialsProviderFactory.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { getLogger, Logger } from '../../shared/logger'
+import { getLogger, Logger } from '../../shared/logger/logger'
 import { loadSharedCredentialsSections, updateAwsSdkLoadConfigEnvVar } from '../credentials/sharedCredentials'
 import { CredentialsProviderType } from './credentials'
 import { BaseCredentialsProviderFactory } from './credentialsProviderFactory'
diff --git a/packages/core/src/auth/secondaryAuth.ts b/packages/core/src/auth/secondaryAuth.ts
index add91765833..01ccf6b799a 100644
--- a/packages/core/src/auth/secondaryAuth.ts
+++ b/packages/core/src/auth/secondaryAuth.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { cast, Optional } from '../shared/utilities/typeConstructors'
 import { Auth } from './auth'
 import { onceChanged } from '../shared/utilities/functionUtils'
diff --git a/packages/core/src/auth/sso/clients.ts b/packages/core/src/auth/sso/clients.ts
index 79ed0db4799..01d0e031d04 100644
--- a/packages/core/src/auth/sso/clients.ts
+++ b/packages/core/src/auth/sso/clients.ts
@@ -26,7 +26,7 @@ import {
 import { AsyncCollection } from '../../shared/utilities/asyncCollection'
 import { pageableToCollection, partialClone } from '../../shared/utilities/collectionUtils'
 import { assertHasProps, isNonNullable, RequiredProps, selectFrom } from '../../shared/utilities/tsUtils'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { SsoAccessTokenProvider } from './ssoAccessTokenProvider'
 import { AwsClientResponseError, isClientFault } from '../../shared/errors'
 import { DevSettings } from '../../shared/settings'
diff --git a/packages/core/src/auth/sso/sdkV2Compat.ts b/packages/core/src/auth/sso/sdkV2Compat.ts
index 0485c023b7f..0ec3f384f32 100644
--- a/packages/core/src/auth/sso/sdkV2Compat.ts
+++ b/packages/core/src/auth/sso/sdkV2Compat.ts
@@ -6,7 +6,7 @@
 import * as AWS from 'aws-sdk'
 import { Token } from 'aws-sdk/lib/token'
 import { Connection } from '../connection'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 
 /**
  * {@link AWS.Token} is defined when {@link Token} is imported.
diff --git a/packages/core/src/auth/sso/server.ts b/packages/core/src/auth/sso/server.ts
index cf25c1456d5..8baf05eb614 100644
--- a/packages/core/src/auth/sso/server.ts
+++ b/packages/core/src/auth/sso/server.ts
@@ -5,7 +5,7 @@
 
 import * as path from 'path'
 import http from 'http'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { ToolkitError } from '../../shared/errors'
 import { Socket } from 'net'
 import globals from '../../shared/extensionGlobals'
diff --git a/packages/core/src/auth/sso/ssoAccessTokenProvider.ts b/packages/core/src/auth/sso/ssoAccessTokenProvider.ts
index 6639e9f3832..5ee8513cbb5 100644
--- a/packages/core/src/auth/sso/ssoAccessTokenProvider.ts
+++ b/packages/core/src/auth/sso/ssoAccessTokenProvider.ts
@@ -21,7 +21,7 @@ import {
     isClientFault,
     isNetworkError,
 } from '../../shared/errors'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { AwsLoginWithBrowser, AwsRefreshCredentials, telemetry } from '../../shared/telemetry/telemetry'
 import { indent, toBase64URL } from '../../shared/utilities/textUtilities'
 import { AuthSSOServer } from './server'
diff --git a/packages/core/src/auth/utils.ts b/packages/core/src/auth/utils.ts
index dd008a55fb4..7c2adbe8086 100644
--- a/packages/core/src/auth/utils.ts
+++ b/packages/core/src/auth/utils.ts
@@ -44,11 +44,10 @@ import {
 import { Commands, placeholder } from '../shared/vscode/commands2'
 import { Auth } from './auth'
 import { validateIsNewSsoUrl, validateSsoUrlFormat } from './sso/validation'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { AuthUtil, isValidAmazonQConnection, isValidCodeWhispererCoreConnection } from '../codewhisperer/util/authUtil'
 import { AuthFormId } from '../login/webview/vue/types'
 import { extensionVersion } from '../shared/vscode/env'
-import { ExtStartUpSources } from '../shared/telemetry'
 import { CommonAuthWebview } from '../login/webview/vue/backend'
 import { AuthSource } from '../login/webview/util'
 import { setContext } from '../shared/vscode/setContext'
@@ -59,7 +58,7 @@ import { EcsCredentialsProvider } from './providers/ecsCredentialsProvider'
 import { EnvVarsCredentialsProvider } from './providers/envVarsCredentialsProvider'
 import { showMessageWithUrl } from '../shared/utilities/messages'
 import { credentialHelpUrl } from '../shared/constants'
-import { ExtStartUpSource } from '../shared/telemetry/util'
+import { ExtStartUpSources, ExtStartUpSource } from '../shared/telemetry/util'
 
 // iam-only excludes Builder ID and IAM Identity Center from the list of valid connections
 // TODO: Understand if "iam" should include these from the list at all
diff --git a/packages/core/src/awsService/accessanalyzer/vue/iamPolicyChecks.ts b/packages/core/src/awsService/accessanalyzer/vue/iamPolicyChecks.ts
index 6123e45f59a..482f2646f3f 100644
--- a/packages/core/src/awsService/accessanalyzer/vue/iamPolicyChecks.ts
+++ b/packages/core/src/awsService/accessanalyzer/vue/iamPolicyChecks.ts
@@ -6,7 +6,7 @@
 import * as vscode from 'vscode'
 import * as fs from 'fs' // eslint-disable-line no-restricted-imports
 import * as path from 'path'
-import { getLogger, Logger } from '../../../shared/logger'
+import { getLogger, Logger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { VueWebview, VueWebviewPanel } from '../../../webviews/main'
 import { ExtContext } from '../../../shared/extensions'
@@ -14,7 +14,7 @@ import { telemetry } from '../../../shared/telemetry/telemetry'
 import { AccessAnalyzer, SharedIniFileCredentials } from 'aws-sdk'
 import { ToolkitError } from '../../../shared/errors'
 import { makeTemporaryToolkitFolder, tryRemoveFolder } from '../../../shared/filesystemUtilities'
-import { globals } from '../../../shared'
+import globals from '../../../shared/extensionGlobals'
 import {
     IamPolicyChecksConstants,
     PolicyChecksCheckType,
diff --git a/packages/core/src/awsService/apigateway/commands/copyUrl.ts b/packages/core/src/awsService/apigateway/commands/copyUrl.ts
index 64a4b75eb13..095d6a916b8 100644
--- a/packages/core/src/awsService/apigateway/commands/copyUrl.ts
+++ b/packages/core/src/awsService/apigateway/commands/copyUrl.ts
@@ -14,7 +14,7 @@ import { ProgressLocation } from 'vscode'
 import { Stage } from 'aws-sdk/clients/apigateway'
 import { DefaultApiGatewayClient } from '../../../shared/clients/apiGatewayClient'
 import { defaultDnsSuffix, RegionProvider } from '../../../shared/regions/regionProvider'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { telemetry } from '../../../shared/telemetry/telemetry'
 
 interface StageInvokeUrlQuickPick extends vscode.QuickPickItem {
diff --git a/packages/core/src/awsService/apigateway/vue/invokeRemoteRestApi.ts b/packages/core/src/awsService/apigateway/vue/invokeRemoteRestApi.ts
index 4d4e015bd59..9eefc0b8b5c 100644
--- a/packages/core/src/awsService/apigateway/vue/invokeRemoteRestApi.ts
+++ b/packages/core/src/awsService/apigateway/vue/invokeRemoteRestApi.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import { RestApiNode } from '../explorer/apiNodes'
-import { getLogger, Logger } from '../../../shared/logger'
+import { getLogger, Logger } from '../../../shared/logger/logger'
 
 import { toArrayAsync } from '../../../shared/utilities/collectionUtils'
 import { Resource } from 'aws-sdk/clients/apigateway'
diff --git a/packages/core/src/awsService/appBuilder/activation.ts b/packages/core/src/awsService/appBuilder/activation.ts
index 9f30282573c..3ee3f9cf171 100644
--- a/packages/core/src/awsService/appBuilder/activation.ts
+++ b/packages/core/src/awsService/appBuilder/activation.ts
@@ -14,7 +14,7 @@ import { setContext } from '../../shared/vscode/setContext'
 import { fs } from '../../shared/fs/fs'
 import { AppBuilderRootNode } from './explorer/nodes/rootNode'
 import { initWalkthroughProjectCommand, walkthroughContextString, getOrInstallCliWrapper } from './walkthrough'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import path from 'path'
 import { TreeNode } from '../../shared/treeview/resourceTreeDataProvider'
 import { runBuild } from '../../shared/sam/build'
diff --git a/packages/core/src/awsService/appBuilder/explorer/nodes/appNode.ts b/packages/core/src/awsService/appBuilder/explorer/nodes/appNode.ts
index d7d5e51bb51..b9c00d59c79 100644
--- a/packages/core/src/awsService/appBuilder/explorer/nodes/appNode.ts
+++ b/packages/core/src/awsService/appBuilder/explorer/nodes/appNode.ts
@@ -7,7 +7,7 @@ import * as nls from 'vscode-nls'
 const localize = nls.loadMessageBundle()
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../../../shared/logger'
+import { getLogger } from '../../../../shared/logger/logger'
 import { ResourceTreeEntity, SamAppLocation, getApp, getStackName } from '../samProject'
 import { ResourceNode, generateResourceNodes } from './resourceNode'
 import { TreeNode } from '../../../../shared/treeview/resourceTreeDataProvider'
diff --git a/packages/core/src/awsService/appBuilder/explorer/nodes/deployedNode.ts b/packages/core/src/awsService/appBuilder/explorer/nodes/deployedNode.ts
index e7181c0d5ba..a5b09bd08de 100644
--- a/packages/core/src/awsService/appBuilder/explorer/nodes/deployedNode.ts
+++ b/packages/core/src/awsService/appBuilder/explorer/nodes/deployedNode.ts
@@ -26,7 +26,7 @@ import {
     SERVERLESS_API_TYPE,
     s3BucketType,
 } from '../../../../shared/cloudformation/cloudformation'
-import { ToolkitError } from '../../../../shared'
+import { ToolkitError } from '../../../../shared/errors'
 
 const localize = nls.loadMessageBundle()
 export interface DeployedResource {
diff --git a/packages/core/src/awsService/appBuilder/explorer/nodes/deployedStack.ts b/packages/core/src/awsService/appBuilder/explorer/nodes/deployedStack.ts
index 76c8f5ea76b..1bf8381e097 100644
--- a/packages/core/src/awsService/appBuilder/explorer/nodes/deployedStack.ts
+++ b/packages/core/src/awsService/appBuilder/explorer/nodes/deployedStack.ts
@@ -6,7 +6,7 @@ import * as vscode from 'vscode'
 import { TreeNode } from '../../../../shared/treeview/resourceTreeDataProvider'
 import { getIcon } from '../../../../shared/icons'
 import { CloudFormationClient, DescribeStacksCommand } from '@aws-sdk/client-cloudformation'
-import { ToolkitError } from '../../../../shared'
+import { ToolkitError } from '../../../../shared/errors'
 import { getIAMConnection } from '../../../../auth/utils'
 
 export class StackNameNode implements TreeNode {
diff --git a/packages/core/src/awsService/appBuilder/walkthrough.ts b/packages/core/src/awsService/appBuilder/walkthrough.ts
index 26760d896aa..098e78584f6 100644
--- a/packages/core/src/awsService/appBuilder/walkthrough.ts
+++ b/packages/core/src/awsService/appBuilder/walkthrough.ts
@@ -6,7 +6,7 @@
 import * as semver from 'semver'
 import * as vscode from 'vscode'
 import globals from '../../shared/extensionGlobals'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 
 import { Wizard } from '../../shared/wizards/wizard'
 import { createQuickPick } from '../../shared/ui/pickerPrompter'
@@ -16,7 +16,7 @@ import { ToolkitError } from '../../shared/errors'
 import { createSingleFileDialog } from '../../shared/ui/common/openDialog'
 import { fs } from '../../shared/fs/fs'
 import path from 'path'
-import { telemetry } from '../../shared/telemetry'
+import { telemetry } from '../../shared/telemetry/telemetry'
 
 import { minSamCliVersionForAppBuilderSupport } from '../../shared/sam/cli/samCliValidator'
 import { SamCliInfoInvocation } from '../../shared/sam/cli/samCliInfo'
diff --git a/packages/core/src/awsService/apprunner/explorer/apprunnerServiceNode.ts b/packages/core/src/awsService/apprunner/explorer/apprunnerServiceNode.ts
index e5c28404d3c..bc8a4e7401f 100644
--- a/packages/core/src/awsService/apprunner/explorer/apprunnerServiceNode.ts
+++ b/packages/core/src/awsService/apprunner/explorer/apprunnerServiceNode.ts
@@ -14,7 +14,7 @@ import { CloudWatchLogs } from 'aws-sdk'
 import { AWSResourceNode } from '../../../shared/treeview/nodes/awsResourceNode'
 
 import * as nls from 'vscode-nls'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { getIcon } from '../../../shared/icons'
 import { DefaultCloudWatchLogsClient } from '../../../shared/clients/cloudWatchLogsClient'
 const localize = nls.loadMessageBundle()
diff --git a/packages/core/src/awsService/cdk/explorer/detectCdkProjects.ts b/packages/core/src/awsService/cdk/explorer/detectCdkProjects.ts
index 55f47f5938f..acf7e28af1a 100644
--- a/packages/core/src/awsService/cdk/explorer/detectCdkProjects.ts
+++ b/packages/core/src/awsService/cdk/explorer/detectCdkProjects.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import * as path from 'path'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { CdkAppLocation } from './cdkProject'
 
 export async function detectCdkProjects(
diff --git a/packages/core/src/awsService/cdk/explorer/nodes/appNode.ts b/packages/core/src/awsService/cdk/explorer/nodes/appNode.ts
index 6c7f4ab76ff..3e79ebba74d 100644
--- a/packages/core/src/awsService/cdk/explorer/nodes/appNode.ts
+++ b/packages/core/src/awsService/cdk/explorer/nodes/appNode.ts
@@ -7,7 +7,7 @@ import * as nls from 'vscode-nls'
 const localize = nls.loadMessageBundle()
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../../../shared/logger'
+import { getLogger } from '../../../../shared/logger/logger'
 import { CdkAppLocation, getApp } from '../cdkProject'
 import { ConstructNode, generateConstructNodes } from './constructNode'
 import { TreeNode } from '../../../../shared/treeview/resourceTreeDataProvider'
diff --git a/packages/core/src/awsService/cloudWatchLogs/activation.ts b/packages/core/src/awsService/cloudWatchLogs/activation.ts
index 5b543ab89ca..4c960bb1d03 100644
--- a/packages/core/src/awsService/cloudWatchLogs/activation.ts
+++ b/packages/core/src/awsService/cloudWatchLogs/activation.ts
@@ -25,7 +25,7 @@ import { LiveTailSessionRegistry } from './registry/liveTailSessionRegistry'
 import { DeployedResourceNode } from '../appBuilder/explorer/nodes/deployedNode'
 import { isTreeNode } from '../../shared/treeview/resourceTreeDataProvider'
 import { getLogger } from '../../shared/logger/logger'
-import { ToolkitError } from '../../shared'
+import { ToolkitError } from '../../shared/errors'
 import { LiveTailCodeLensProvider } from './document/liveTailCodeLensProvider'
 
 export const liveTailRegistry = LiveTailSessionRegistry.instance
diff --git a/packages/core/src/awsService/cloudWatchLogs/commands/searchLogGroup.ts b/packages/core/src/awsService/cloudWatchLogs/commands/searchLogGroup.ts
index 41ce8d7922f..3ece0923dec 100644
--- a/packages/core/src/awsService/cloudWatchLogs/commands/searchLogGroup.ts
+++ b/packages/core/src/awsService/cloudWatchLogs/commands/searchLogGroup.ts
@@ -19,7 +19,7 @@ import { isValidResponse, isWizardControl, Wizard, WIZARD_RETRY } from '../../..
 import { cwlUriSchema, msgKey, recordTelemetryFilter } from '../cloudWatchLogsUtils'
 import { DefaultCloudWatchLogsClient } from '../../../shared/clients/cloudWatchLogsClient'
 import { CancellationError } from '../../../shared/utilities/timeoutUtils'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { TimeFilterResponse, TimeFilterSubmenu } from '../timeFilterSubmenu'
 import { CloudWatchLogs } from 'aws-sdk'
 import { ExtendedInputBoxOptions, InputBox, InputBoxPrompter } from '../../../shared/ui/inputPrompter'
diff --git a/packages/core/src/awsService/cloudWatchLogs/commands/tailLogGroup.ts b/packages/core/src/awsService/cloudWatchLogs/commands/tailLogGroup.ts
index 210104f7a31..a86ed4d3382 100644
--- a/packages/core/src/awsService/cloudWatchLogs/commands/tailLogGroup.ts
+++ b/packages/core/src/awsService/cloudWatchLogs/commands/tailLogGroup.ts
@@ -14,7 +14,9 @@ import {
     LiveTailSessionUpdate,
     StartLiveTailResponseStream,
 } from '@aws-sdk/client-cloudwatch-logs'
-import { getLogger, globals, ToolkitError } from '../../../shared'
+import { ToolkitError } from '../../../shared/errors'
+import { getLogger } from '../../../shared/logger/logger'
+import globals from '../../../shared/extensionGlobals'
 import { uriToKey } from '../cloudWatchLogsUtils'
 import { LiveTailCodeLensProvider } from '../document/liveTailCodeLensProvider'
 import { LogStreamFilterResponse } from '../wizard/liveTailLogStreamSubmenu'
diff --git a/packages/core/src/awsService/cloudWatchLogs/document/logDataDocumentProvider.ts b/packages/core/src/awsService/cloudWatchLogs/document/logDataDocumentProvider.ts
index 5925911893b..f54a8b12391 100644
--- a/packages/core/src/awsService/cloudWatchLogs/document/logDataDocumentProvider.ts
+++ b/packages/core/src/awsService/cloudWatchLogs/document/logDataDocumentProvider.ts
@@ -4,7 +4,7 @@
  */
 import * as vscode from 'vscode'
 import { CloudWatchLogsGroupInfo, LogDataRegistry, UriString } from '../registry/logDataRegistry'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { generateTextFromLogEvents, LineToLogStreamMap } from './textContent'
 import { cwlUriSchema } from '../cloudWatchLogsUtils'
 
diff --git a/packages/core/src/awsService/cloudWatchLogs/registry/liveTailSession.ts b/packages/core/src/awsService/cloudWatchLogs/registry/liveTailSession.ts
index 87eba4d4079..6ec785e76c6 100644
--- a/packages/core/src/awsService/cloudWatchLogs/registry/liveTailSession.ts
+++ b/packages/core/src/awsService/cloudWatchLogs/registry/liveTailSession.ts
@@ -11,7 +11,9 @@ import {
 } from '@aws-sdk/client-cloudwatch-logs'
 import { LogStreamFilterResponse } from '../wizard/liveTailLogStreamSubmenu'
 import { CloudWatchLogsSettings } from '../cloudWatchLogsUtils'
-import { globals, Settings, ToolkitError } from '../../../shared'
+import globals from '../../../shared/extensionGlobals'
+import { Settings } from '../../../shared/settings'
+import { ToolkitError } from '../../../shared/errors'
 import { createLiveTailURIFromArgs } from './liveTailSessionRegistry'
 import { getUserAgent } from '../../../shared/telemetry/util'
 import { convertToTimeString } from '../../../shared/datetime'
diff --git a/packages/core/src/awsService/cloudWatchLogs/wizard/tailLogGroupWizard.ts b/packages/core/src/awsService/cloudWatchLogs/wizard/tailLogGroupWizard.ts
index b9c14829dab..d2039686fc4 100644
--- a/packages/core/src/awsService/cloudWatchLogs/wizard/tailLogGroupWizard.ts
+++ b/packages/core/src/awsService/cloudWatchLogs/wizard/tailLogGroupWizard.ts
@@ -4,7 +4,8 @@
  */
 
 import * as nls from 'vscode-nls'
-import { globals, ToolkitError } from '../../../shared'
+import globals from '../../../shared/extensionGlobals'
+import { ToolkitError } from '../../../shared/errors'
 import { DefaultCloudWatchLogsClient } from '../../../shared/clients/cloudWatchLogsClient'
 import { cwlFilterPatternHelpUrl } from '../../../shared/constants'
 import { createBackButton, createExitButton, createHelpButton } from '../../../shared/ui/buttons'
diff --git a/packages/core/src/awsService/ec2/connectionManagerMap.ts b/packages/core/src/awsService/ec2/connectionManagerMap.ts
index add39f05bea..fa1a258fa2f 100644
--- a/packages/core/src/awsService/ec2/connectionManagerMap.ts
+++ b/packages/core/src/awsService/ec2/connectionManagerMap.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { getLogger } from '../../shared'
+import { getLogger } from '../../shared/logger/logger'
 import { Ec2Connecter } from './model'
 
 export class Ec2ConnecterMap extends Map<string, Ec2Connecter> {
diff --git a/packages/core/src/awsService/ec2/explorer/ec2InstanceNode.ts b/packages/core/src/awsService/ec2/explorer/ec2InstanceNode.ts
index d00fe55e9c2..e6d0ab4113d 100644
--- a/packages/core/src/awsService/ec2/explorer/ec2InstanceNode.ts
+++ b/packages/core/src/awsService/ec2/explorer/ec2InstanceNode.ts
@@ -12,7 +12,7 @@ import { getIconCode } from '../utils'
 import { Ec2Selection } from '../prompter'
 import { Ec2Node, Ec2ParentNode } from './ec2ParentNode'
 import { EC2 } from 'aws-sdk'
-import { getLogger } from '../../../shared'
+import { getLogger } from '../../../shared/logger/logger'
 
 export const Ec2InstanceRunningContext = 'awsEc2RunningNode'
 export const Ec2InstanceStoppedContext = 'awsEc2StoppedNode'
diff --git a/packages/core/src/awsService/ec2/sshKeyPair.ts b/packages/core/src/awsService/ec2/sshKeyPair.ts
index 369c14964c7..cb67ca39ba1 100644
--- a/packages/core/src/awsService/ec2/sshKeyPair.ts
+++ b/packages/core/src/awsService/ec2/sshKeyPair.ts
@@ -3,7 +3,8 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 import os from 'os'
-import { fs, globals } from '../../shared'
+import globals from '../../shared/extensionGlobals'
+import { fs } from '../../shared/fs/fs'
 import { ToolkitError } from '../../shared/errors'
 import { tryRun } from '../../shared/utilities/pathFind'
 import { Timeout } from '../../shared/utilities/timeoutUtils'
diff --git a/packages/core/src/awsService/ec2/utils.ts b/packages/core/src/awsService/ec2/utils.ts
index 105d2da06ff..e54f4dfb970 100644
--- a/packages/core/src/awsService/ec2/utils.ts
+++ b/packages/core/src/awsService/ec2/utils.ts
@@ -8,7 +8,7 @@ import { copyToClipboard } from '../../shared/utilities/messages'
 import { Ec2Selection } from './prompter'
 import { sshLogFileLocation } from '../../shared/sshConfig'
 import { SSM } from 'aws-sdk'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 
 export function getIconCode(instance: SafeEc2Instance) {
     if (instance.LastSeenStatus === 'running') {
diff --git a/packages/core/src/awsService/ecr/commands/createRepository.ts b/packages/core/src/awsService/ecr/commands/createRepository.ts
index 5f26409f6e0..d2c75ff3c46 100644
--- a/packages/core/src/awsService/ecr/commands/createRepository.ts
+++ b/packages/core/src/awsService/ecr/commands/createRepository.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { EcrNode } from '../explorer/ecrNode'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage } from '../../../shared/utilities/messages'
diff --git a/packages/core/src/awsService/ecr/commands/deleteRepository.ts b/packages/core/src/awsService/ecr/commands/deleteRepository.ts
index aa258e00633..ec14841d0d6 100644
--- a/packages/core/src/awsService/ecr/commands/deleteRepository.ts
+++ b/packages/core/src/awsService/ecr/commands/deleteRepository.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { EcrRepositoryNode } from '../explorer/ecrRepositoryNode'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage } from '../../../shared/utilities/messages'
diff --git a/packages/core/src/awsService/ecr/commands/deleteTag.ts b/packages/core/src/awsService/ecr/commands/deleteTag.ts
index 86f153f0062..a037db0934b 100644
--- a/packages/core/src/awsService/ecr/commands/deleteTag.ts
+++ b/packages/core/src/awsService/ecr/commands/deleteTag.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import { EcrTagNode } from '../explorer/ecrTagNode'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { showConfirmationMessage, showViewLogsMessage } from '../../../shared/utilities/messages'
 import { telemetry } from '../../../shared/telemetry/telemetry'
diff --git a/packages/core/src/awsService/ecs/util.ts b/packages/core/src/awsService/ecs/util.ts
index 7996107e481..db506c33867 100644
--- a/packages/core/src/awsService/ecs/util.ts
+++ b/packages/core/src/awsService/ecs/util.ts
@@ -14,7 +14,7 @@ import { ToolkitError } from '../../shared/errors'
 import { isCloud9 } from '../../shared/extensionUtilities'
 import { getOrInstallCli } from '../../shared/utilities/cliUtils'
 import { Session, TaskDefinition } from 'aws-sdk/clients/ecs'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { SSM } from 'aws-sdk'
 import { fromExtensionManifest } from '../../shared/settings'
 import { ecsTaskPermissionsUrl } from '../../shared/constants'
diff --git a/packages/core/src/awsService/iot/commands/attachCertificate.ts b/packages/core/src/awsService/iot/commands/attachCertificate.ts
index c77f1d36d44..be9edd03d89 100644
--- a/packages/core/src/awsService/iot/commands/attachCertificate.ts
+++ b/packages/core/src/awsService/iot/commands/attachCertificate.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { IotThingNode } from '../explorer/iotThingNode'
 import { showViewLogsMessage } from '../../../shared/utilities/messages'
diff --git a/packages/core/src/awsService/iot/commands/attachPolicy.ts b/packages/core/src/awsService/iot/commands/attachPolicy.ts
index 6eb6f721790..e9d40f1528b 100644
--- a/packages/core/src/awsService/iot/commands/attachPolicy.ts
+++ b/packages/core/src/awsService/iot/commands/attachPolicy.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage } from '../../../shared/utilities/messages'
 import { createQuickPick, DataQuickPickItem } from '../../../shared/ui/pickerPrompter'
diff --git a/packages/core/src/awsService/iot/commands/copyEndpoint.ts b/packages/core/src/awsService/iot/commands/copyEndpoint.ts
index 64c9f5462de..0846250c5cb 100644
--- a/packages/core/src/awsService/iot/commands/copyEndpoint.ts
+++ b/packages/core/src/awsService/iot/commands/copyEndpoint.ts
@@ -7,7 +7,7 @@ import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { IotNode } from '../explorer/iotNodes'
 import { showViewLogsMessage } from '../../../shared/utilities/messages'
 import { copyToClipboard } from '../../../shared/utilities/messages'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 
 /**
  * Copies the path to the folder or file represented by the given node.
diff --git a/packages/core/src/awsService/iot/commands/createCert.ts b/packages/core/src/awsService/iot/commands/createCert.ts
index 3f6eae413db..c954de28886 100644
--- a/packages/core/src/awsService/iot/commands/createCert.ts
+++ b/packages/core/src/awsService/iot/commands/createCert.ts
@@ -5,13 +5,13 @@
 
 import * as vscode from 'vscode'
 import * as path from 'path'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage } from '../../../shared/utilities/messages'
 import { IotCertsFolderNode } from '../explorer/iotCertFolderNode'
 import { fileExists } from '../../../shared/filesystemUtilities'
 import { Iot } from 'aws-sdk'
-import { fs } from '../../../shared'
+import { fs } from '../../../shared/fs/fs'
 
 // eslint-disable-next-line @typescript-eslint/naming-convention
 const MODE_RW_R_R = 0o644 // File permission 0644 rw-r--r-- for PEM files.
diff --git a/packages/core/src/awsService/iot/commands/createPolicy.ts b/packages/core/src/awsService/iot/commands/createPolicy.ts
index ba082811e34..1bb04618d7f 100644
--- a/packages/core/src/awsService/iot/commands/createPolicy.ts
+++ b/packages/core/src/awsService/iot/commands/createPolicy.ts
@@ -4,11 +4,11 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage } from '../../../shared/utilities/messages'
 import { IotPolicyFolderNode } from '../explorer/iotPolicyFolderNode'
-import { fs } from '../../../shared'
+import { fs } from '../../../shared/fs/fs'
 
 /**
  * Creates a policy from a policy document.
diff --git a/packages/core/src/awsService/iot/commands/createPolicyVersion.ts b/packages/core/src/awsService/iot/commands/createPolicyVersion.ts
index 257626489f6..4719277a5ec 100644
--- a/packages/core/src/awsService/iot/commands/createPolicyVersion.ts
+++ b/packages/core/src/awsService/iot/commands/createPolicyVersion.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage } from '../../../shared/utilities/messages'
 import { IotPolicyWithVersionsNode } from '../explorer/iotPolicyNode'
diff --git a/packages/core/src/awsService/iot/commands/createThing.ts b/packages/core/src/awsService/iot/commands/createThing.ts
index 2d9b1f11d4e..8909d894911 100644
--- a/packages/core/src/awsService/iot/commands/createThing.ts
+++ b/packages/core/src/awsService/iot/commands/createThing.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage } from '../../../shared/utilities/messages'
 import { IotThingFolderNode } from '../explorer/iotThingFolderNode'
diff --git a/packages/core/src/awsService/iot/commands/deleteCert.ts b/packages/core/src/awsService/iot/commands/deleteCert.ts
index 058dd8ae4d8..592bbb66339 100644
--- a/packages/core/src/awsService/iot/commands/deleteCert.ts
+++ b/packages/core/src/awsService/iot/commands/deleteCert.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import * as localizedText from '../../../shared/localizedText'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage, showConfirmationMessage } from '../../../shared/utilities/messages'
 import { IotCertWithPoliciesNode } from '../explorer/iotCertificateNode'
diff --git a/packages/core/src/awsService/iot/commands/deletePolicy.ts b/packages/core/src/awsService/iot/commands/deletePolicy.ts
index 80ff20b6727..4d09ffd0a26 100644
--- a/packages/core/src/awsService/iot/commands/deletePolicy.ts
+++ b/packages/core/src/awsService/iot/commands/deletePolicy.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import * as localizedText from '../../../shared/localizedText'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { IotPolicyWithVersionsNode } from '../explorer/iotPolicyNode'
 import { showViewLogsMessage, showConfirmationMessage } from '../../../shared/utilities/messages'
diff --git a/packages/core/src/awsService/iot/commands/deletePolicyVersion.ts b/packages/core/src/awsService/iot/commands/deletePolicyVersion.ts
index 4dbfd4fcde3..b34708c4ee2 100644
--- a/packages/core/src/awsService/iot/commands/deletePolicyVersion.ts
+++ b/packages/core/src/awsService/iot/commands/deletePolicyVersion.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import * as localizedText from '../../../shared/localizedText'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage, showConfirmationMessage } from '../../../shared/utilities/messages'
 import { IotPolicyVersionNode } from '../explorer/iotPolicyVersionNode'
diff --git a/packages/core/src/awsService/iot/commands/deleteThing.ts b/packages/core/src/awsService/iot/commands/deleteThing.ts
index d96aa92a35b..4aecb0d126a 100644
--- a/packages/core/src/awsService/iot/commands/deleteThing.ts
+++ b/packages/core/src/awsService/iot/commands/deleteThing.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import * as localizedText from '../../../shared/localizedText'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { IotThingNode } from '../explorer/iotThingNode'
 import { showViewLogsMessage, showConfirmationMessage } from '../../../shared/utilities/messages'
diff --git a/packages/core/src/awsService/iot/commands/detachCert.ts b/packages/core/src/awsService/iot/commands/detachCert.ts
index a8384e34b79..536869894dc 100644
--- a/packages/core/src/awsService/iot/commands/detachCert.ts
+++ b/packages/core/src/awsService/iot/commands/detachCert.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import * as localizedText from '../../../shared/localizedText'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { IotThingCertNode } from '../explorer/iotCertificateNode'
 import { showViewLogsMessage, showConfirmationMessage } from '../../../shared/utilities/messages'
diff --git a/packages/core/src/awsService/iot/commands/detachPolicy.ts b/packages/core/src/awsService/iot/commands/detachPolicy.ts
index 9370b450f59..a85ad8fe5a2 100644
--- a/packages/core/src/awsService/iot/commands/detachPolicy.ts
+++ b/packages/core/src/awsService/iot/commands/detachPolicy.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import * as localizedText from '../../../shared/localizedText'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage, showConfirmationMessage } from '../../../shared/utilities/messages'
 import { IotPolicyCertNode } from '../explorer/iotPolicyNode'
diff --git a/packages/core/src/awsService/iot/commands/setDefaultPolicy.ts b/packages/core/src/awsService/iot/commands/setDefaultPolicy.ts
index 355c79cf96f..8e406719bff 100644
--- a/packages/core/src/awsService/iot/commands/setDefaultPolicy.ts
+++ b/packages/core/src/awsService/iot/commands/setDefaultPolicy.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { IotPolicyVersionNode } from '../explorer/iotPolicyVersionNode'
 import { showViewLogsMessage } from '../../../shared/utilities/messages'
diff --git a/packages/core/src/awsService/iot/commands/updateCert.ts b/packages/core/src/awsService/iot/commands/updateCert.ts
index a6e9d1ecd74..53a7aa34181 100644
--- a/packages/core/src/awsService/iot/commands/updateCert.ts
+++ b/packages/core/src/awsService/iot/commands/updateCert.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import * as localizedText from '../../../shared/localizedText'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { IotCertificateNode } from '../explorer/iotCertificateNode'
 import { showViewLogsMessage, showConfirmationMessage } from '../../../shared/utilities/messages'
diff --git a/packages/core/src/awsService/iot/commands/viewPolicyVersion.ts b/packages/core/src/awsService/iot/commands/viewPolicyVersion.ts
index 1d788257ace..a6c33bbeb86 100644
--- a/packages/core/src/awsService/iot/commands/viewPolicyVersion.ts
+++ b/packages/core/src/awsService/iot/commands/viewPolicyVersion.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { getTabSizeSetting } from '../../../shared/utilities/editorUtilities'
 import { IotPolicyVersionNode } from '../explorer/iotPolicyVersionNode'
 import { showViewLogsMessage } from '../../../shared/utilities/messages'
diff --git a/packages/core/src/awsService/iot/explorer/iotCertFolderNode.ts b/packages/core/src/awsService/iot/explorer/iotCertFolderNode.ts
index 98c1b664f78..240da3136f4 100644
--- a/packages/core/src/awsService/iot/explorer/iotCertFolderNode.ts
+++ b/packages/core/src/awsService/iot/explorer/iotCertFolderNode.ts
@@ -13,7 +13,7 @@ import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { ChildNodeLoader } from '../../../awsexplorer/childNodeLoader'
 import { ChildNodePage } from '../../../awsexplorer/childNodeLoader'
 import { inspect } from 'util'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { IotCertWithPoliciesNode } from './iotCertificateNode'
 import { IotNode } from './iotNodes'
 import { Settings } from '../../../shared/settings'
diff --git a/packages/core/src/awsService/iot/explorer/iotCertificateNode.ts b/packages/core/src/awsService/iot/explorer/iotCertificateNode.ts
index d77becff9bb..a90afec36b5 100644
--- a/packages/core/src/awsService/iot/explorer/iotCertificateNode.ts
+++ b/packages/core/src/awsService/iot/explorer/iotCertificateNode.ts
@@ -15,7 +15,7 @@ import { makeChildrenNodes } from '../../../shared/treeview/utils'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { ChildNodeLoader } from '../../../awsexplorer/childNodeLoader'
 import { inspect } from 'util'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { IotCertsFolderNode } from './iotCertFolderNode'
 import { IotThingNode } from './iotThingNode'
 import { IotPolicyCertNode } from './iotPolicyNode'
diff --git a/packages/core/src/awsService/iot/explorer/iotPolicyFolderNode.ts b/packages/core/src/awsService/iot/explorer/iotPolicyFolderNode.ts
index 36af63cf495..ed7a39270d5 100644
--- a/packages/core/src/awsService/iot/explorer/iotPolicyFolderNode.ts
+++ b/packages/core/src/awsService/iot/explorer/iotPolicyFolderNode.ts
@@ -13,7 +13,7 @@ import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { ChildNodeLoader } from '../../../awsexplorer/childNodeLoader'
 import { ChildNodePage } from '../../../awsexplorer/childNodeLoader'
 import { inspect } from 'util'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { IotPolicyWithVersionsNode } from './iotPolicyNode'
 import { IotNode } from './iotNodes'
 import { Settings } from '../../../shared/settings'
diff --git a/packages/core/src/awsService/iot/explorer/iotThingFolderNode.ts b/packages/core/src/awsService/iot/explorer/iotThingFolderNode.ts
index 1965047712d..e3dee64c896 100644
--- a/packages/core/src/awsService/iot/explorer/iotThingFolderNode.ts
+++ b/packages/core/src/awsService/iot/explorer/iotThingFolderNode.ts
@@ -14,7 +14,7 @@ import { ChildNodeLoader } from '../../../awsexplorer/childNodeLoader'
 import { ChildNodePage } from '../../../awsexplorer/childNodeLoader'
 import { IotThingNode } from './iotThingNode'
 import { inspect } from 'util'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { IotNode } from './iotNodes'
 import { Settings } from '../../../shared/settings'
 import { ClassToInterfaceType } from '../../../shared/utilities/tsUtils'
diff --git a/packages/core/src/awsService/iot/explorer/iotThingNode.ts b/packages/core/src/awsService/iot/explorer/iotThingNode.ts
index ad40a6e1411..c6bc14014a3 100644
--- a/packages/core/src/awsService/iot/explorer/iotThingNode.ts
+++ b/packages/core/src/awsService/iot/explorer/iotThingNode.ts
@@ -15,7 +15,7 @@ import { makeChildrenNodes } from '../../../shared/treeview/utils'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { ChildNodeLoader } from '../../../awsexplorer/childNodeLoader'
 import { inspect } from 'util'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { IotThingFolderNode } from './iotThingFolderNode'
 import { IotThingCertNode } from './iotCertificateNode'
 import { getIcon } from '../../../shared/icons'
diff --git a/packages/core/src/awsService/redshift/messageUtils.ts b/packages/core/src/awsService/redshift/messageUtils.ts
index edd470c2d32..a1e8420b84d 100644
--- a/packages/core/src/awsService/redshift/messageUtils.ts
+++ b/packages/core/src/awsService/redshift/messageUtils.ts
@@ -4,7 +4,7 @@
  */
 
 import globals from '../../shared/extensionGlobals'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { showViewLogsMessage } from '../../shared/utilities/messages'
 
 /**
diff --git a/packages/core/src/awsService/s3/commands/createBucket.ts b/packages/core/src/awsService/s3/commands/createBucket.ts
index 82313cb8379..cd451a9da5e 100644
--- a/packages/core/src/awsService/s3/commands/createBucket.ts
+++ b/packages/core/src/awsService/s3/commands/createBucket.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { S3Node } from '../explorer/s3Nodes'
 import { validateBucketName } from '../util'
diff --git a/packages/core/src/awsService/s3/commands/createFolder.ts b/packages/core/src/awsService/s3/commands/createFolder.ts
index 785aff0ad48..370f55a32b4 100644
--- a/packages/core/src/awsService/s3/commands/createFolder.ts
+++ b/packages/core/src/awsService/s3/commands/createFolder.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import { DEFAULT_DELIMITER } from '../../../shared/clients/s3Client'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { S3BucketNode } from '../explorer/s3BucketNode'
 import { S3FolderNode } from '../explorer/s3FolderNode'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
diff --git a/packages/core/src/awsService/s3/commands/deleteBucket.ts b/packages/core/src/awsService/s3/commands/deleteBucket.ts
index c2f9818b718..b5d5b3f115c 100644
--- a/packages/core/src/awsService/s3/commands/deleteBucket.ts
+++ b/packages/core/src/awsService/s3/commands/deleteBucket.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { S3BucketNode } from '../explorer/s3BucketNode'
 import { S3Node } from '../explorer/s3Nodes'
diff --git a/packages/core/src/awsService/s3/commands/deleteFile.ts b/packages/core/src/awsService/s3/commands/deleteFile.ts
index 7b0f86eabde..cb54331b3aa 100644
--- a/packages/core/src/awsService/s3/commands/deleteFile.ts
+++ b/packages/core/src/awsService/s3/commands/deleteFile.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import * as localizedText from '../../../shared/localizedText'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { addCodiconToString } from '../../../shared/utilities/textUtilities'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
 import { S3BucketNode } from '../explorer/s3BucketNode'
diff --git a/packages/core/src/awsService/s3/commands/uploadFile.ts b/packages/core/src/awsService/s3/commands/uploadFile.ts
index 41093a96f2f..1adf7f0e7ab 100644
--- a/packages/core/src/awsService/s3/commands/uploadFile.ts
+++ b/packages/core/src/awsService/s3/commands/uploadFile.ts
@@ -8,7 +8,7 @@ import * as mime from 'mime-types'
 import * as vscode from 'vscode'
 import { statSync } from 'fs' // eslint-disable-line no-restricted-imports
 import { S3 } from 'aws-sdk'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { S3Node } from '../explorer/s3Nodes'
 import { readablePath } from '../util'
 import { localize } from '../../../shared/utilities/vsCodeUtils'
diff --git a/packages/core/src/awsService/s3/commands/uploadFileToParent.ts b/packages/core/src/awsService/s3/commands/uploadFileToParent.ts
index 037512a074d..211ceb326e6 100644
--- a/packages/core/src/awsService/s3/commands/uploadFileToParent.ts
+++ b/packages/core/src/awsService/s3/commands/uploadFileToParent.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { S3FileNode } from '../explorer/s3FileNode'
 import { uploadFileCommand } from './uploadFile'
 
diff --git a/packages/core/src/awsService/s3/explorer/s3BucketNode.ts b/packages/core/src/awsService/s3/explorer/s3BucketNode.ts
index c24efee9deb..253edde2f67 100644
--- a/packages/core/src/awsService/s3/explorer/s3BucketNode.ts
+++ b/packages/core/src/awsService/s3/explorer/s3BucketNode.ts
@@ -17,7 +17,7 @@ import { ChildNodeLoader } from '../../../awsexplorer/childNodeLoader'
 import { S3FileNode } from './s3FileNode'
 import { S3FolderNode } from './s3FolderNode'
 import { inspect } from 'util'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { S3Node } from './s3Nodes'
 import { getIcon } from '../../../shared/icons'
 import { Settings } from '../../../shared/settings'
diff --git a/packages/core/src/awsService/s3/explorer/s3FolderNode.ts b/packages/core/src/awsService/s3/explorer/s3FolderNode.ts
index d8c5ea4c0d9..0553250c731 100644
--- a/packages/core/src/awsService/s3/explorer/s3FolderNode.ts
+++ b/packages/core/src/awsService/s3/explorer/s3FolderNode.ts
@@ -15,7 +15,7 @@ import { ChildNodeLoader } from '../../../awsexplorer/childNodeLoader'
 import { ChildNodePage } from '../../../awsexplorer/childNodeLoader'
 import { S3FileNode } from './s3FileNode'
 import { inspect } from 'util'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { getIcon } from '../../../shared/icons'
 import { Settings } from '../../../shared/settings'
 import { ClassToInterfaceType } from '../../../shared/utilities/tsUtils'
diff --git a/packages/core/src/awsService/s3/fileViewerManager.ts b/packages/core/src/awsService/s3/fileViewerManager.ts
index d800a3bfeee..730ceb90c28 100644
--- a/packages/core/src/awsService/s3/fileViewerManager.ts
+++ b/packages/core/src/awsService/s3/fileViewerManager.ts
@@ -7,7 +7,7 @@ import * as path from 'path'
 import * as vscode from 'vscode'
 import * as mime from 'mime-types'
 import * as S3 from '../../shared/clients/s3Client'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { showConfirmationMessage } from '../../shared/utilities/messages'
 import { localize, openUrl } from '../../shared/utilities/vsCodeUtils'
 import { CancellationError } from '../../shared/utilities/timeoutUtils'
diff --git a/packages/core/src/awsexplorer/activation.ts b/packages/core/src/awsexplorer/activation.ts
index 224bbadb2fb..4452648019e 100644
--- a/packages/core/src/awsexplorer/activation.ts
+++ b/packages/core/src/awsexplorer/activation.ts
@@ -9,7 +9,7 @@ import { CloudFormationStackNode } from '../lambda/explorer/cloudFormationNodes'
 import globals from '../shared/extensionGlobals'
 import { isCloud9, isSageMaker } from '../shared/extensionUtilities'
 import { ExtContext, VSCODE_EXTENSION_ID } from '../shared/extensions'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { RegionProvider } from '../shared/regions/regionProvider'
 import { AWSResourceNode } from '../shared/treeview/nodes/awsResourceNode'
 import { AWSTreeNodeBase } from '../shared/treeview/nodes/awsTreeNodeBase'
@@ -29,9 +29,9 @@ import { CodeCatalystAuthenticationProvider } from '../codecatalyst/auth'
 import { S3FolderNode } from '../awsService/s3/explorer/s3FolderNode'
 import { AmazonQNode, refreshAmazonQ, refreshAmazonQRootNode } from '../amazonq/explorer/amazonQTreeNode'
 import { activateViewsShared, registerToolView } from './activationShared'
-import { isExtensionInstalled } from '../shared/utilities'
-import { CommonAuthViewProvider } from '../login/webview'
-import { setContext } from '../shared'
+import { isExtensionInstalled } from '../shared/utilities/vsCodeUtils'
+import { CommonAuthViewProvider } from '../login/webview/commonAuthViewProvider'
+import { setContext } from '../shared/vscode/setContext'
 import { TreeNode } from '../shared/treeview/resourceTreeDataProvider'
 import { getSourceNode } from '../shared/utilities/treeNodeUtils'
 import { openAwsCFNConsoleCommand, openAwsConsoleCommand } from '../shared/awsConsole'
diff --git a/packages/core/src/awsexplorer/awsExplorer.ts b/packages/core/src/awsexplorer/awsExplorer.ts
index fb4b1b455df..63707527173 100644
--- a/packages/core/src/awsexplorer/awsExplorer.ts
+++ b/packages/core/src/awsexplorer/awsExplorer.ts
@@ -7,7 +7,7 @@ import * as vscode from 'vscode'
 import { Auth } from '../auth/auth'
 import { getIdeProperties } from '../shared/extensionUtilities'
 import { getIcon } from '../shared/icons'
-import { getLogger, Logger } from '../shared/logger'
+import { getLogger, Logger } from '../shared/logger/logger'
 import { RegionProvider } from '../shared/regions/regionProvider'
 import { RefreshableAwsTreeProvider } from '../shared/treeview/awsTreeProvider'
 import { AWSCommandTreeNode } from '../shared/treeview/nodes/awsCommandTreeNode'
diff --git a/packages/core/src/awsexplorer/commands/loadMoreChildren.ts b/packages/core/src/awsexplorer/commands/loadMoreChildren.ts
index 9d256664792..6bc37b770e2 100644
--- a/packages/core/src/awsexplorer/commands/loadMoreChildren.ts
+++ b/packages/core/src/awsexplorer/commands/loadMoreChildren.ts
@@ -4,7 +4,7 @@
  */
 
 import { localize } from '../../shared/utilities/vsCodeUtils'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { AWSTreeNodeBase } from '../../shared/treeview/nodes/awsTreeNodeBase'
 import { LoadMoreNode } from '../../shared/treeview/nodes/loadMoreNode'
 import { AwsExplorer } from '../awsExplorer'
diff --git a/packages/core/src/codecatalyst/auth.ts b/packages/core/src/codecatalyst/auth.ts
index 11e31a37c4f..f1d3ea82954 100644
--- a/packages/core/src/codecatalyst/auth.ts
+++ b/packages/core/src/codecatalyst/auth.ts
@@ -8,7 +8,7 @@ import { onAccessDeniedException, CodeCatalystClient, createClient } from '../sh
 import { Auth } from '../auth/auth'
 import * as localizedText from '../shared/localizedText'
 import { getSecondaryAuth, setScopes } from '../auth/secondaryAuth'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import globals from '../shared/extensionGlobals'
 import { ToolkitError, isAwsError } from '../shared/errors'
 import { MetricName, MetricShapes, telemetry } from '../shared/telemetry/telemetry'
diff --git a/packages/core/src/codecatalyst/devEnv.ts b/packages/core/src/codecatalyst/devEnv.ts
index 44db151d8de..962c772eb2f 100644
--- a/packages/core/src/codecatalyst/devEnv.ts
+++ b/packages/core/src/codecatalyst/devEnv.ts
@@ -8,7 +8,7 @@ import { DevEnvActivity, DevEnvClient } from '../shared/clients/devenvClient'
 import globals from '../shared/extensionGlobals'
 import * as vscode from 'vscode'
 import { waitUntil } from '../shared/utilities/timeoutUtils'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { CodeCatalystAuthenticationProvider } from './auth'
 import { getThisDevEnv } from './model'
 import { isInDevEnv } from '../shared/vscode/env'
diff --git a/packages/core/src/codecatalyst/devfile.ts b/packages/core/src/codecatalyst/devfile.ts
index 851a706b157..f8a857e2555 100644
--- a/packages/core/src/codecatalyst/devfile.ts
+++ b/packages/core/src/codecatalyst/devfile.ts
@@ -10,7 +10,7 @@ import * as vscode from 'vscode'
 import * as path from 'path'
 import { DevEnvClient } from '../shared/clients/devenvClient'
 import { DevfileRegistry, devfileGlobPattern } from '../shared/fs/devfileRegistry'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { Commands } from '../shared/vscode/commands2'
 import { checkUnsavedChanges } from '../shared/utilities/workspaceUtils'
 import { ToolkitError } from '../shared/errors'
diff --git a/packages/core/src/codecatalyst/explorer.ts b/packages/core/src/codecatalyst/explorer.ts
index d20fcc6d37d..af3d6a20474 100644
--- a/packages/core/src/codecatalyst/explorer.ts
+++ b/packages/core/src/codecatalyst/explorer.ts
@@ -12,7 +12,7 @@ import { CodeCatalystAuthenticationProvider } from './auth'
 import { CodeCatalystCommands, codecatalystConnectionsCmd } from './commands'
 import { ConnectedDevEnv, getDevfileLocation, getThisDevEnv } from './model'
 import * as codecatalyst from './model'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { SsoConnection } from '../auth/connection'
 import { openUrl } from '../shared/utilities/vsCodeUtils'
 
diff --git a/packages/core/src/codecatalyst/model.ts b/packages/core/src/codecatalyst/model.ts
index d49d8780cde..0451f9be95b 100644
--- a/packages/core/src/codecatalyst/model.ts
+++ b/packages/core/src/codecatalyst/model.ts
@@ -15,7 +15,7 @@ import {
     getCodeCatalystConfig,
 } from '../shared/clients/codecatalystClient'
 import { DevEnvClient } from '../shared/clients/devenvClient'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { AsyncCollection, toCollection } from '../shared/utilities/asyncCollection'
 import { getCodeCatalystSpaceName, getCodeCatalystProjectName, getCodeCatalystDevEnvId } from '../shared/vscode/env'
 import { sshAgentSocketVariable, startSshAgent, startVscodeRemote } from '../shared/extensions/ssh'
@@ -29,7 +29,7 @@ import { ToolkitError } from '../shared/errors'
 import { Result } from '../shared/utilities/result'
 import { EnvProvider, VscodeRemoteConnection, createBoundProcess, ensureDependencies } from '../shared/remoteSession'
 import { SshConfig, sshLogFileLocation } from '../shared/sshConfig'
-import { fs } from '../shared'
+import { fs } from '../shared/fs/fs'
 
 export type DevEnvironmentId = Pick<DevEnvironment, 'id' | 'org' | 'project'>
 export const connectScriptPrefix = 'codecatalyst_connect'
diff --git a/packages/core/src/codecatalyst/reconnect.ts b/packages/core/src/codecatalyst/reconnect.ts
index ecedbd3eb04..9e0ab491f38 100644
--- a/packages/core/src/codecatalyst/reconnect.ts
+++ b/packages/core/src/codecatalyst/reconnect.ts
@@ -7,7 +7,7 @@ import * as nls from 'vscode-nls'
 import * as vscode from 'vscode'
 import { CodeCatalystClient, createClient, DevEnvironment } from '../shared/clients/codecatalystClient'
 import { ExtContext } from '../shared/extensions'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { sleep } from '../shared/utilities/timeoutUtils'
 import { DevEnvironmentSettings } from './commands'
 import { codeCatalystConnectCommand, DevEnvironmentId, DevEnvMemento } from './model'
diff --git a/packages/core/src/codecatalyst/uriHandlers.ts b/packages/core/src/codecatalyst/uriHandlers.ts
index b34dd25761b..7e4f9080519 100644
--- a/packages/core/src/codecatalyst/uriHandlers.ts
+++ b/packages/core/src/codecatalyst/uriHandlers.ts
@@ -8,7 +8,7 @@ import { SearchParams, UriHandler } from '../shared/vscode/uriHandler'
 import { getCodeCatalystConfig } from '../shared/clients/codecatalystClient'
 import { CodeCatalystCommands } from './commands'
 import { defaultSsoRegion } from '../auth/connection'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { builderIdStartUrl } from '../auth/sso/constants'
 
 type ConnectParams = {
diff --git a/packages/core/src/codecatalyst/utils.ts b/packages/core/src/codecatalyst/utils.ts
index 6a704ddeb07..b28aea75d4d 100644
--- a/packages/core/src/codecatalyst/utils.ts
+++ b/packages/core/src/codecatalyst/utils.ts
@@ -7,7 +7,7 @@ import { Ides } from 'aws-sdk/clients/codecatalyst'
 import * as vscode from 'vscode'
 import { CodeCatalystResource, getCodeCatalystConfig } from '../shared/clients/codecatalystClient'
 import { pushIf } from '../shared/utilities/collectionUtils'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 
 /**
  * Builds a web URL from the given CodeCatalyst object.
diff --git a/packages/core/src/codewhisperer/activation.ts b/packages/core/src/codewhisperer/activation.ts
index 30efb21e0b2..3ab3b89c65a 100644
--- a/packages/core/src/codewhisperer/activation.ts
+++ b/packages/core/src/codewhisperer/activation.ts
@@ -26,7 +26,7 @@ import { ExtContext } from '../shared/extensions'
 import { CodeWhispererTracker } from './tracker/codewhispererTracker'
 import * as codewhispererClient from './client/codewhisperer'
 import { runtimeLanguageContext } from './util/runtimeLanguageContext'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import {
     enableCodeSuggestions,
     toggleCodeSuggestions,
@@ -90,7 +90,7 @@ import { securityScanLanguageContext } from './util/securityScanLanguageContext'
 import { registerWebviewErrorHandler } from '../webviews/server'
 import { logAndShowError, logAndShowWebviewError } from '../shared/utilities/logAndShowUtils'
 import { openSettings } from '../shared/settings'
-import { telemetry } from '../shared/telemetry'
+import { telemetry } from '../shared/telemetry/telemetry'
 import { FeatureConfigProvider } from '../shared/featureConfig'
 import { SecurityIssueProvider } from './service/securityIssueProvider'
 import { SecurityIssueTreeViewProvider } from './service/securityIssueTreeViewProvider'
diff --git a/packages/core/src/codewhisperer/client/agent.ts b/packages/core/src/codewhisperer/client/agent.ts
index 52152d2a616..6df3629fbed 100644
--- a/packages/core/src/codewhisperer/client/agent.ts
+++ b/packages/core/src/codewhisperer/client/agent.ts
@@ -14,7 +14,7 @@
 import * as vscode from 'vscode'
 import http from 'http'
 import https from 'https'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 
 // The path to the exported class can be found in the npm contents
 // https://www.npmjs.com/package/@vscode/proxy-agent?activeTab=code
diff --git a/packages/core/src/codewhisperer/client/codewhisperer.ts b/packages/core/src/codewhisperer/client/codewhisperer.ts
index ceaf020fb02..68331c53ef4 100644
--- a/packages/core/src/codewhisperer/client/codewhisperer.ts
+++ b/packages/core/src/codewhisperer/client/codewhisperer.ts
@@ -18,7 +18,7 @@ import { pageableToCollection } from '../../shared/utilities/collectionUtils'
 import apiConfig = require('./service-2.json')
 import userApiConfig = require('./user-service-2.json')
 import { CodeWhispererSessionState } from '../util/codeWhispererSession'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { indent } from '../../shared/utilities/textUtilities'
 import { keepAliveHeader } from './agent'
 import { getClientId, getOptOutPreference, getOperatingSystem } from '../../shared/telemetry/util'
diff --git a/packages/core/src/codewhisperer/commands/basicCommands.ts b/packages/core/src/codewhisperer/commands/basicCommands.ts
index 3693bbd4d6c..364d8b07e4e 100644
--- a/packages/core/src/codewhisperer/commands/basicCommands.ts
+++ b/packages/core/src/codewhisperer/commands/basicCommands.ts
@@ -27,7 +27,7 @@ import { connectToEnterpriseSso, getStartUrl } from '../util/getStartUrl'
 import { showCodeWhispererConnectionPrompt } from '../util/showSsoPrompt'
 import { ReferenceLogViewProvider } from '../service/referenceLogViewProvider'
 import { AuthUtil } from '../util/authUtil'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { isExtensionActive, isExtensionInstalled, localize, openUrl } from '../../shared/utilities/vsCodeUtils'
 import {
     getPersistedCustomizations,
@@ -44,7 +44,8 @@ import {
 import { Mutable } from '../../shared/utilities/tsUtils'
 import { CodeWhispererSource } from './types'
 import { TelemetryHelper } from '../util/telemetryHelper'
-import { Auth, AwsConnection } from '../../auth'
+import { Auth } from '../../auth/auth'
+import { AwsConnection } from '../../auth/connection'
 import { once } from '../../shared/utilities/functionUtils'
 import { focusAmazonQPanel } from '../../codewhispererChat/commands/registerCommands'
 import { removeDiagnostic } from '../service/diagnosticsProvider'
@@ -61,13 +62,13 @@ import { SecurityIssueProvider } from '../service/securityIssueProvider'
 import { CodeWhispererSettings } from '../util/codewhispererSettings'
 import { closeDiff, getPatchedCode } from '../../shared/utilities/diffUtils'
 import { insertCommentAboveLine } from '../../shared/utilities/commentUtils'
-import { cancel, confirm } from '../../shared'
 import { startCodeFixGeneration } from './startCodeFixGeneration'
 import { DefaultAmazonQAppInitContext } from '../../amazonq/apps/initContext'
 import path from 'path'
 import { UserWrittenCodeTracker } from '../tracker/userWrittenCodeTracker'
 import { parsePatch } from 'diff'
 import { createCodeIssueGroupingStrategyPrompter } from '../ui/prompters'
+import { cancel, confirm } from '../../shared/localizedText'
 
 const MessageTimeOut = 5_000
 
diff --git a/packages/core/src/codewhisperer/commands/onInlineAcceptance.ts b/packages/core/src/codewhisperer/commands/onInlineAcceptance.ts
index a9a888ef8c4..a0845892dbe 100644
--- a/packages/core/src/codewhisperer/commands/onInlineAcceptance.ts
+++ b/packages/core/src/codewhisperer/commands/onInlineAcceptance.ts
@@ -30,7 +30,7 @@ import { CodeWhispererSessionState } from '../util/codeWhispererSession'
 import path from 'path'
 import { RecommendationService } from '../service/recommendationService'
 import { Container } from '../service/serviceContainer'
-import { telemetry } from '../../shared/telemetry'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { TelemetryHelper } from '../util/telemetryHelper'
 import { UserWrittenCodeTracker } from '../tracker/userWrittenCodeTracker'
 
diff --git a/packages/core/src/codewhisperer/commands/startCodeFixGeneration.ts b/packages/core/src/codewhisperer/commands/startCodeFixGeneration.ts
index 32566c259e3..a255864c7eb 100644
--- a/packages/core/src/codewhisperer/commands/startCodeFixGeneration.ts
+++ b/packages/core/src/codewhisperer/commands/startCodeFixGeneration.ts
@@ -2,7 +2,8 @@
  * Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
  * SPDX-License-Identifier: Apache-2.0
  */
-import { fs, getLogger, tempDirPath } from '../../shared'
+import { fs } from '../../shared/fs/fs'
+import { getLogger } from '../../shared/logger/logger'
 import {
     createCodeFixJob,
     getCodeFixJob,
@@ -16,6 +17,7 @@ import { CreateCodeFixError } from '../models/errors'
 import AdmZip from 'adm-zip'
 import path from 'path'
 import { TelemetryHelper } from '../util/telemetryHelper'
+import { tempDirPath } from '../../shared/filesystemUtilities'
 
 export async function startCodeFixGeneration(
     client: DefaultCodeWhispererClient,
diff --git a/packages/core/src/codewhisperer/commands/startSecurityScan.ts b/packages/core/src/codewhisperer/commands/startSecurityScan.ts
index 8c222f83760..5aef9184e2e 100644
--- a/packages/core/src/codewhisperer/commands/startSecurityScan.ts
+++ b/packages/core/src/codewhisperer/commands/startSecurityScan.ts
@@ -8,7 +8,7 @@ import * as nls from 'vscode-nls'
 import { ArtifactMap, DefaultCodeWhispererClient } from '../client/codewhisperer'
 import { initSecurityScanRender } from '../service/diagnosticsProvider'
 import { SecurityPanelViewProvider } from '../views/securityPanelViewProvider'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { makeLogger } from '../../shared/logger/activation'
 import * as CodeWhispererConstants from '../models/constants'
 import {
diff --git a/packages/core/src/codewhisperer/commands/startTestGeneration.ts b/packages/core/src/codewhisperer/commands/startTestGeneration.ts
index 429e3585d36..c394310d4f8 100644
--- a/packages/core/src/codewhisperer/commands/startTestGeneration.ts
+++ b/packages/core/src/codewhisperer/commands/startTestGeneration.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { ZipUtil } from '../util/zipUtil'
 import { ArtifactMap } from '../client/codewhisperer'
 import { testGenerationLogsDir } from '../../shared/filesystemUtilities'
diff --git a/packages/core/src/codewhisperer/commands/startTransformByQ.ts b/packages/core/src/codewhisperer/commands/startTransformByQ.ts
index cec513d4f58..d6428836d71 100644
--- a/packages/core/src/codewhisperer/commands/startTransformByQ.ts
+++ b/packages/core/src/codewhisperer/commands/startTransformByQ.ts
@@ -6,7 +6,7 @@
 import * as vscode from 'vscode'
 import * as fs from 'fs' // eslint-disable-line no-restricted-imports
 import path from 'path'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import * as CodeWhispererConstants from '../models/constants'
 import * as localizedText from '../../shared/localizedText'
 import {
@@ -76,10 +76,10 @@ import DependencyVersions from '../../amazonqGumby/models/dependencies'
 import { dependencyNoAvailableVersions } from '../../amazonqGumby/models/constants'
 import { HumanInTheLoopManager } from '../service/transformByQ/humanInTheLoopManager'
 import { setContext } from '../../shared/vscode/setContext'
-import { makeTemporaryToolkitFolder } from '../../shared'
 import globals from '../../shared/extensionGlobals'
 import { convertDateToTimestamp } from '../../shared/datetime'
 import { findStringInDirectory } from '../../shared/utilities/workspaceUtils'
+import { makeTemporaryToolkitFolder } from '../../shared/filesystemUtilities'
 
 function getFeedbackCommentData() {
     const jobId = transformByQState.getJobId()
diff --git a/packages/core/src/codewhisperer/models/errors.ts b/packages/core/src/codewhisperer/models/errors.ts
index 9466fede54d..cce4aa04a75 100644
--- a/packages/core/src/codewhisperer/models/errors.ts
+++ b/packages/core/src/codewhisperer/models/errors.ts
@@ -2,8 +2,8 @@
  * Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
  * SPDX-License-Identifier: Apache-2.0
  */
-import { i18n } from '../../shared'
 import { ToolkitError } from '../../shared/errors'
+import { i18n } from '../../shared/i18n-helper'
 import {
     DefaultCodeScanErrorMessage,
     FileSizeExceededErrorMessage,
diff --git a/packages/core/src/codewhisperer/service/codeFixHandler.ts b/packages/core/src/codewhisperer/service/codeFixHandler.ts
index e260f3808ea..854cb848a52 100644
--- a/packages/core/src/codewhisperer/service/codeFixHandler.ts
+++ b/packages/core/src/codewhisperer/service/codeFixHandler.ts
@@ -6,7 +6,6 @@
 import { CodeWhispererUserClient } from '../indexNode'
 import * as CodeWhispererConstants from '../models/constants'
 import { codeFixState } from '../models/model'
-import { getLogger, isAwsError, sleep } from '../../shared'
 import { ArtifactMap, CreateUploadUrlRequest, DefaultCodeWhispererClient } from '../client/codewhisperer'
 import {
     CodeFixJobStoppedError,
@@ -16,6 +15,9 @@ import {
     MonthlyCodeFixLimitError,
 } from '../models/errors'
 import { uploadArtifactToS3 } from './securityScanHandler'
+import { getLogger } from '../../shared/logger/logger'
+import { isAwsError } from '../../shared/errors'
+import { sleep } from '../../shared/utilities/timeoutUtils'
 
 export async function getPresignedUrlAndUpload(
     client: DefaultCodeWhispererClient,
diff --git a/packages/core/src/codewhisperer/service/keyStrokeHandler.ts b/packages/core/src/codewhisperer/service/keyStrokeHandler.ts
index d32e875e8a4..49ef633a98f 100644
--- a/packages/core/src/codewhisperer/service/keyStrokeHandler.ts
+++ b/packages/core/src/codewhisperer/service/keyStrokeHandler.ts
@@ -7,7 +7,7 @@ import * as vscode from 'vscode'
 import { DefaultCodeWhispererClient } from '../client/codewhisperer'
 import * as CodeWhispererConstants from '../models/constants'
 import { ConfigurationEntry } from '../models/model'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { RecommendationHandler } from './recommendationHandler'
 import { CodewhispererAutomatedTriggerType } from '../../shared/telemetry/telemetry'
 import { getTabSizeSetting } from '../../shared/utilities/editorUtilities'
diff --git a/packages/core/src/codewhisperer/service/recommendationHandler.ts b/packages/core/src/codewhisperer/service/recommendationHandler.ts
index 92595df2fdb..bdbf21074bd 100644
--- a/packages/core/src/codewhisperer/service/recommendationHandler.ts
+++ b/packages/core/src/codewhisperer/service/recommendationHandler.ts
@@ -18,7 +18,7 @@ import { runtimeLanguageContext } from '../util/runtimeLanguageContext'
 import { AWSError } from 'aws-sdk'
 import { isAwsError } from '../../shared/errors'
 import { TelemetryHelper } from '../util/telemetryHelper'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { hasVendedIamCredentials } from '../../auth/auth'
 import {
     asyncCallWithTimeout,
diff --git a/packages/core/src/codewhisperer/service/referenceInlineProvider.ts b/packages/core/src/codewhisperer/service/referenceInlineProvider.ts
index 9e2382837ff..a90565797fb 100644
--- a/packages/core/src/codewhisperer/service/referenceInlineProvider.ts
+++ b/packages/core/src/codewhisperer/service/referenceInlineProvider.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import * as CodeWhispererConstants from '../models/constants'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { References } from '../client/codewhisperer'
 import { LicenseUtil } from '../util/licenseUtil'
 import { isInlineCompletionEnabled } from '../util/commonUtil'
diff --git a/packages/core/src/codewhisperer/service/securityIssueTreeViewProvider.ts b/packages/core/src/codewhisperer/service/securityIssueTreeViewProvider.ts
index 197f5f15fd2..9b803a4033c 100644
--- a/packages/core/src/codewhisperer/service/securityIssueTreeViewProvider.ts
+++ b/packages/core/src/codewhisperer/service/securityIssueTreeViewProvider.ts
@@ -13,7 +13,7 @@ import {
     Severity,
 } from '../models/model'
 import globals from '../../shared/extensionGlobals'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { SecurityIssueProvider } from './securityIssueProvider'
 
 export type SecurityViewTreeItem = FileItem | IssueItem | SeverityItem
diff --git a/packages/core/src/codewhisperer/service/securityScanHandler.ts b/packages/core/src/codewhisperer/service/securityScanHandler.ts
index a8db65603b3..cf344610e27 100644
--- a/packages/core/src/codewhisperer/service/securityScanHandler.ts
+++ b/packages/core/src/codewhisperer/service/securityScanHandler.ts
@@ -4,7 +4,7 @@
  */
 
 import { DefaultCodeWhispererClient } from '../client/codewhisperer'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import * as vscode from 'vscode'
 import {
     AggregatedCodeScanIssue,
diff --git a/packages/core/src/codewhisperer/service/testGenHandler.ts b/packages/core/src/codewhisperer/service/testGenHandler.ts
index 48a66fb1f83..fd5c07606e8 100644
--- a/packages/core/src/codewhisperer/service/testGenHandler.ts
+++ b/packages/core/src/codewhisperer/service/testGenHandler.ts
@@ -4,7 +4,7 @@
  */
 
 import { ZipMetadata } from '../util/zipUtil'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import * as CodeWhispererConstants from '../models/constants'
 import * as codewhispererClient from '../client/codewhisperer'
 import * as codeWhisperer from '../client/codewhisperer'
@@ -23,7 +23,6 @@ import {
     TestGenTimedOutError,
 } from '../../amazonqTest/error'
 import { getMd5, uploadArtifactToS3 } from './securityScanHandler'
-import { fs, randomUUID, sleep, tempDirPath } from '../../shared'
 import { ShortAnswer, testGenState } from '../models/model'
 import { ChatSessionManager } from '../../amazonqTest/chat/storages/chatSession'
 import { createCodeWhispererChatStreamingClient } from '../../shared/clients/codewhispererChatClient'
@@ -33,6 +32,10 @@ import path from 'path'
 import { ExportIntent } from '@amzn/codewhisperer-streaming'
 import { glob } from 'glob'
 import { UserWrittenCodeTracker } from '../tracker/userWrittenCodeTracker'
+import { randomUUID } from '../../shared/crypto'
+import { sleep } from '../../shared/utilities/timeoutUtils'
+import { tempDirPath } from '../../shared/filesystemUtilities'
+import fs from '../../shared/fs/fs'
 
 // TODO: Get TestFileName and Framework and to error message
 export function throwIfCancelled() {
diff --git a/packages/core/src/codewhisperer/service/transformByQ/humanInTheLoopManager.ts b/packages/core/src/codewhisperer/service/transformByQ/humanInTheLoopManager.ts
index 0402483656d..63c1bfe3a2f 100644
--- a/packages/core/src/codewhisperer/service/transformByQ/humanInTheLoopManager.ts
+++ b/packages/core/src/codewhisperer/service/transformByQ/humanInTheLoopManager.ts
@@ -9,8 +9,8 @@ import { FolderInfo, transformByQState } from '../../models/model'
 import fs from '../../../shared/fs/fs'
 import { createPomCopy, replacePomVersion } from './transformFileHandler'
 import { IManifestFile } from '../../../amazonqFeatureDev/models'
-import { getLogger } from '../../../shared/logger'
-import { telemetry } from '../../../shared/telemetry'
+import { getLogger } from '../../../shared/logger/logger'
+import { telemetry } from '../../../shared/telemetry/telemetry'
 import { CodeTransformTelemetryState } from '../../../amazonqGumby/telemetry/codeTransformTelemetryState'
 import { MetadataResult } from '../../../shared/telemetry/telemetryClient'
 
diff --git a/packages/core/src/codewhisperer/service/transformByQ/transformApiHandler.ts b/packages/core/src/codewhisperer/service/transformByQ/transformApiHandler.ts
index b24db799b3a..1ba9b4681c8 100644
--- a/packages/core/src/codewhisperer/service/transformByQ/transformApiHandler.ts
+++ b/packages/core/src/codewhisperer/service/transformByQ/transformApiHandler.ts
@@ -22,7 +22,7 @@ import {
     TransformByQStoppedError,
     ZipManifest,
 } from '../../models/model'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import {
     CreateUploadUrlResponse,
     ProgressUpdates,
diff --git a/packages/core/src/codewhisperer/service/transformByQ/transformFileHandler.ts b/packages/core/src/codewhisperer/service/transformByQ/transformFileHandler.ts
index 767869d0310..c2a0617c15f 100644
--- a/packages/core/src/codewhisperer/service/transformByQ/transformFileHandler.ts
+++ b/packages/core/src/codewhisperer/service/transformByQ/transformFileHandler.ts
@@ -15,7 +15,7 @@ import fs from '../../../shared/fs/fs'
 import globals from '../../../shared/extensionGlobals'
 import { ChatSessionManager } from '../../../amazonqGumby/chat/storages/chatSession'
 import { AbsolutePathDetectedError } from '../../../amazonqGumby/errors'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { isWin } from '../../../shared/vscode/env'
 
 export function getDependenciesFolderInfo(): FolderInfo {
diff --git a/packages/core/src/codewhisperer/service/transformByQ/transformMavenHandler.ts b/packages/core/src/codewhisperer/service/transformByQ/transformMavenHandler.ts
index e2bbbc6556b..3384d8f2781 100644
--- a/packages/core/src/codewhisperer/service/transformByQ/transformMavenHandler.ts
+++ b/packages/core/src/codewhisperer/service/transformByQ/transformMavenHandler.ts
@@ -4,7 +4,7 @@
  */
 import * as vscode from 'vscode'
 import { FolderInfo, transformByQState } from '../../models/model'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import * as CodeWhispererConstants from '../../models/constants'
 // Consider using ChildProcess once we finalize all spawnSync calls
 import { spawnSync } from 'child_process' // eslint-disable-line no-restricted-imports
diff --git a/packages/core/src/codewhisperer/service/transformByQ/transformationHubViewProvider.ts b/packages/core/src/codewhisperer/service/transformByQ/transformationHubViewProvider.ts
index ef2ce722598..63eae8606bb 100644
--- a/packages/core/src/codewhisperer/service/transformByQ/transformationHubViewProvider.ts
+++ b/packages/core/src/codewhisperer/service/transformByQ/transformationHubViewProvider.ts
@@ -13,7 +13,7 @@ import {
     sessionJobHistory,
     transformByQState,
 } from '../../models/model'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { getTransformationSteps } from './transformApiHandler'
 import {
     TransformationSteps,
diff --git a/packages/core/src/codewhisperer/service/transformByQ/transformationResultsViewProvider.ts b/packages/core/src/codewhisperer/service/transformByQ/transformationResultsViewProvider.ts
index 9339be10fc9..b7878222caf 100644
--- a/packages/core/src/codewhisperer/service/transformByQ/transformationResultsViewProvider.ts
+++ b/packages/core/src/codewhisperer/service/transformByQ/transformationResultsViewProvider.ts
@@ -18,7 +18,7 @@ import {
     TransformationType,
 } from '../../models/model'
 import { ExportResultArchiveStructure, downloadExportResultArchive } from '../../../shared/utilities/download'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { telemetry } from '../../../shared/telemetry/telemetry'
 import { CodeTransformTelemetryState } from '../../../amazonqGumby/telemetry/codeTransformTelemetryState'
 import * as CodeWhispererConstants from '../../models/constants'
diff --git a/packages/core/src/codewhisperer/tracker/codewhispererTracker.ts b/packages/core/src/codewhisperer/tracker/codewhispererTracker.ts
index 05a6d83f3f0..dbcfb3ab134 100644
--- a/packages/core/src/codewhisperer/tracker/codewhispererTracker.ts
+++ b/packages/core/src/codewhisperer/tracker/codewhispererTracker.ts
@@ -15,7 +15,8 @@ import { codeWhispererClient } from '../client/codewhisperer'
 import { logSendTelemetryEventFailure } from '../../codewhispererChat/controllers/chat/telemetryHelper'
 import { Timeout } from '../../shared/utilities/timeoutUtils'
 import { getSelectedCustomization } from '../util/customizationUtil'
-import { isAwsError, undefinedIfEmpty } from '../../shared'
+import { isAwsError } from '../../shared/errors'
+import { undefinedIfEmpty } from '../../shared/utilities/textUtilities'
 import { getUnmodifiedAcceptedTokens } from '../util/commonUtil'
 
 /**
diff --git a/packages/core/src/codewhisperer/tracker/lineTracker.ts b/packages/core/src/codewhisperer/tracker/lineTracker.ts
index b7ca091b541..7fce5ef9534 100644
--- a/packages/core/src/codewhisperer/tracker/lineTracker.ts
+++ b/packages/core/src/codewhisperer/tracker/lineTracker.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import { isTextEditor } from '../../shared/utilities/editorUtilities'
-import { setContext } from '../../shared'
+import { setContext } from '../../shared/vscode/setContext'
 
 export interface LineSelection {
     anchor: number
diff --git a/packages/core/src/codewhisperer/tracker/userWrittenCodeTracker.ts b/packages/core/src/codewhisperer/tracker/userWrittenCodeTracker.ts
index 2497006b0a4..32de471878d 100644
--- a/packages/core/src/codewhisperer/tracker/userWrittenCodeTracker.ts
+++ b/packages/core/src/codewhisperer/tracker/userWrittenCodeTracker.ts
@@ -10,7 +10,9 @@ import { AuthUtil } from '../util/authUtil'
 import { getSelectedCustomization } from '../util/customizationUtil'
 import { codeWhispererClient as client } from '../client/codewhisperer'
 import { isAwsError } from '../../shared/errors'
-import { CodewhispererLanguage, globals, undefinedIfEmpty } from '../../shared'
+import { undefinedIfEmpty } from '../../shared/utilities/textUtilities'
+import { CodewhispererLanguage } from '../../shared/telemetry/telemetry'
+import globals from '../../shared/extensionGlobals'
 
 /**
  * This singleton class is mainly used for calculating the user written code
diff --git a/packages/core/src/codewhisperer/ui/statusBarMenu.ts b/packages/core/src/codewhisperer/ui/statusBarMenu.ts
index 8988f0eb339..9b5fa43672e 100644
--- a/packages/core/src/codewhisperer/ui/statusBarMenu.ts
+++ b/packages/core/src/codewhisperer/ui/statusBarMenu.ts
@@ -29,7 +29,7 @@ import { CodeScansState, CodeSuggestionsState, vsCodeState } from '../models/mod
 import { Commands } from '../../shared/vscode/commands2'
 import { createExitButton } from '../../shared/ui/buttons'
 import { telemetry } from '../../shared/telemetry/telemetry'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 
 function getAmazonQCodeWhispererNodes() {
     const autoTriggerEnabled = CodeSuggestionsState.instance.isSuggestionsEnabled()
diff --git a/packages/core/src/codewhisperer/util/authUtil.ts b/packages/core/src/codewhisperer/util/authUtil.ts
index 1a94ad5ffcc..1e350384e73 100644
--- a/packages/core/src/codewhisperer/util/authUtil.ts
+++ b/packages/core/src/codewhisperer/util/authUtil.ts
@@ -28,7 +28,7 @@ import {
     getTelemetryMetadataForConn,
     ProfileNotFoundError,
 } from '../../auth/connection'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { Commands, placeholder } from '../../shared/vscode/commands2'
 import { vsCodeState } from '../models/model'
 import { onceChanged, once } from '../../shared/utilities/functionUtils'
diff --git a/packages/core/src/codewhisperer/util/customizationUtil.ts b/packages/core/src/codewhisperer/util/customizationUtil.ts
index 0ede7c983f9..9bacb06c48a 100644
--- a/packages/core/src/codewhisperer/util/customizationUtil.ts
+++ b/packages/core/src/codewhisperer/util/customizationUtil.ts
@@ -13,7 +13,7 @@ import { DataQuickPickItem, showQuickPick } from '../../shared/ui/pickerPrompter
 import { codeWhispererClient } from '../client/codewhisperer'
 import { Customization, ResourceArn } from '../client/codewhispereruserclient'
 import { codicon, getIcon } from '../../shared/icons'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { showMessageWithUrl } from '../../shared/utilities/messages'
 import { parse } from '@aws-sdk/util-arn-parser'
 import { Commands } from '../../shared/vscode/commands2'
diff --git a/packages/core/src/codewhisperer/util/editorContext.ts b/packages/core/src/codewhisperer/util/editorContext.ts
index 99a15fd1f02..11598cfe20c 100644
--- a/packages/core/src/codewhisperer/util/editorContext.ts
+++ b/packages/core/src/codewhisperer/util/editorContext.ts
@@ -17,7 +17,7 @@ import { selectFrom } from '../../shared/utilities/tsUtils'
 import { checkLeftContextKeywordsForJson } from './commonUtil'
 import { CodeWhispererSupplementalContext } from '../models/model'
 import { getOptOutPreference } from '../../shared/telemetry/util'
-import { indent } from '../../shared'
+import { indent } from '../../shared/utilities/textUtilities'
 
 let tabSize: number = getTabSizeSetting()
 
diff --git a/packages/core/src/codewhisperer/util/gitUtil.ts b/packages/core/src/codewhisperer/util/gitUtil.ts
index 752c16ba6bf..09cd9a6116f 100644
--- a/packages/core/src/codewhisperer/util/gitUtil.ts
+++ b/packages/core/src/codewhisperer/util/gitUtil.ts
@@ -3,7 +3,8 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { getLogger, removeAnsi } from '../../shared'
+import { removeAnsi } from '../../shared/utilities/textUtilities'
+import { getLogger } from '../../shared/logger/logger'
 import { ChildProcess, ChildProcessOptions } from '../../shared/utilities/processUtils'
 import { Uri } from 'vscode'
 
diff --git a/packages/core/src/codewhisperer/util/showSsoPrompt.ts b/packages/core/src/codewhisperer/util/showSsoPrompt.ts
index 229583a8cc2..13af4cf771f 100644
--- a/packages/core/src/codewhisperer/util/showSsoPrompt.ts
+++ b/packages/core/src/codewhisperer/util/showSsoPrompt.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { getStartUrl } from './getStartUrl'
 import { showQuickPick } from '../../shared/ui/pickerPrompter'
 import { AuthUtil } from './authUtil'
diff --git a/packages/core/src/codewhisperer/util/supplementalContext/crossFileContextUtil.ts b/packages/core/src/codewhisperer/util/supplementalContext/crossFileContextUtil.ts
index f4688e2b5a9..db1d7f312b2 100644
--- a/packages/core/src/codewhisperer/util/supplementalContext/crossFileContextUtil.ts
+++ b/packages/core/src/codewhisperer/util/supplementalContext/crossFileContextUtil.ts
@@ -4,7 +4,6 @@
  */
 
 import * as vscode from 'vscode'
-import { FeatureConfigProvider, fs } from '../../../shared'
 import path = require('path')
 import { BM25Document, BM25Okapi } from './rankBm25'
 import {
@@ -23,6 +22,8 @@ import {
 } from '../../models/model'
 import { LspController } from '../../../amazonq/lsp/lspController'
 import { waitUntil } from '../../../shared/utilities/timeoutUtils'
+import { FeatureConfigProvider } from '../../../shared/featureConfig'
+import fs from '../../../shared/fs/fs'
 
 type CrossFileSupportedLanguage =
     | 'java'
diff --git a/packages/core/src/codewhisperer/util/supplementalContext/utgUtils.ts b/packages/core/src/codewhisperer/util/supplementalContext/utgUtils.ts
index a39a48183b0..0d33969773e 100644
--- a/packages/core/src/codewhisperer/util/supplementalContext/utgUtils.ts
+++ b/packages/core/src/codewhisperer/util/supplementalContext/utgUtils.ts
@@ -4,7 +4,7 @@
  */
 
 import * as path from 'path'
-import { fs } from '../../../shared'
+import { fs } from '../../../shared/fs/fs'
 import * as vscode from 'vscode'
 import {
     countSubstringMatches,
diff --git a/packages/core/src/codewhisperer/util/telemetryHelper.ts b/packages/core/src/codewhisperer/util/telemetryHelper.ts
index 964145fd881..22ece4400d2 100644
--- a/packages/core/src/codewhisperer/util/telemetryHelper.ts
+++ b/packages/core/src/codewhisperer/util/telemetryHelper.ts
@@ -21,7 +21,7 @@ import { CodeWhispererSettings } from './codewhispererSettings'
 import { getSelectedCustomization } from './customizationUtil'
 import { AuthUtil } from './authUtil'
 import { isAwsError } from '../../shared/errors'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { CodeWhispererSessionState } from './codeWhispererSession'
 import { CodeWhispererSupplementalContext } from '../models/model'
 import { FeatureConfigProvider } from '../../shared/featureConfig'
diff --git a/packages/core/src/codewhisperer/util/zipUtil.ts b/packages/core/src/codewhisperer/util/zipUtil.ts
index 64a9ccc3b8d..18379e051ad 100644
--- a/packages/core/src/codewhisperer/util/zipUtil.ts
+++ b/packages/core/src/codewhisperer/util/zipUtil.ts
@@ -6,7 +6,7 @@ import admZip from 'adm-zip'
 import * as vscode from 'vscode'
 import path from 'path'
 import { tempDirPath, testGenerationLogsDir } from '../../shared/filesystemUtilities'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import * as CodeWhispererConstants from '../models/constants'
 import { ToolkitError } from '../../shared/errors'
 import { fs } from '../../shared/fs/fs'
@@ -22,8 +22,8 @@ import {
 } from '../models/errors'
 import { FeatureUseCase } from '../models/constants'
 import { ChildProcess, ChildProcessOptions } from '../../shared/utilities/processUtils'
-import { removeAnsi } from '../../shared'
 import { ProjectZipError } from '../../amazonqTest/error'
+import { removeAnsi } from '../../shared/utilities/textUtilities'
 
 export interface ZipMetadata {
     rootDir: string
diff --git a/packages/core/src/codewhisperer/views/activeStateController.ts b/packages/core/src/codewhisperer/views/activeStateController.ts
index 184498f3f4a..b3c991a9d38 100644
--- a/packages/core/src/codewhisperer/views/activeStateController.ts
+++ b/packages/core/src/codewhisperer/views/activeStateController.ts
@@ -11,7 +11,7 @@ import { subscribeOnce } from '../../shared/utilities/vsCodeUtils'
 import { Container } from '../service/serviceContainer'
 import { RecommendationHandler } from '../service/recommendationHandler'
 import { cancellableDebounce } from '../../shared/utilities/functionUtils'
-import { telemetry } from '../../shared/telemetry'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { TelemetryHelper } from '../util/telemetryHelper'
 
 export class ActiveStateController implements vscode.Disposable {
diff --git a/packages/core/src/codewhisperer/views/lineAnnotationController.ts b/packages/core/src/codewhisperer/views/lineAnnotationController.ts
index 39732c84064..7cf51a39f9c 100644
--- a/packages/core/src/codewhisperer/views/lineAnnotationController.ts
+++ b/packages/core/src/codewhisperer/views/lineAnnotationController.ts
@@ -19,7 +19,7 @@ import { Commands } from '../../shared/vscode/commands2'
 import { CodeWhispererSessionState } from '../util/codeWhispererSession'
 import { RecommendationHandler } from '../service/recommendationHandler'
 import { runtimeLanguageContext } from '../util/runtimeLanguageContext'
-import { setContext } from '../../shared'
+import { setContext } from '../../shared/vscode/setContext'
 import { TelemetryHelper } from '../util/telemetryHelper'
 
 const case3TimeWindow = 30000 // 30 seconds
diff --git a/packages/core/src/codewhisperer/vue/backend.ts b/packages/core/src/codewhisperer/vue/backend.ts
index f92552e247a..0f4701fb745 100644
--- a/packages/core/src/codewhisperer/vue/backend.ts
+++ b/packages/core/src/codewhisperer/vue/backend.ts
@@ -10,8 +10,8 @@ import * as path from 'path'
 import { VueWebview } from '../../webviews/main'
 import globals from '../../shared/extensionGlobals'
 import { telemetry, CodewhispererLanguage, CodewhispererGettingStartedTask } from '../../shared/telemetry/telemetry'
-import { fs } from '../../shared'
-import { getLogger } from '../../shared/logger'
+import { fs } from '../../shared/fs/fs'
+import { getLogger } from '../../shared/logger/logger'
 import { AmazonQPromptSettings } from '../../shared/settings'
 import { CodeWhispererSource } from '../commands/types'
 import { submitFeedback } from '../../feedback/vue/submitFeedback'
diff --git a/packages/core/src/codewhispererChat/controllers/chat/chatRequest/converter.ts b/packages/core/src/codewhispererChat/controllers/chat/chatRequest/converter.ts
index a3236f7d402..c30d5aeb706 100644
--- a/packages/core/src/codewhispererChat/controllers/chat/chatRequest/converter.ts
+++ b/packages/core/src/codewhispererChat/controllers/chat/chatRequest/converter.ts
@@ -12,7 +12,7 @@ import {
     TextDocument,
 } from '@amzn/codewhisperer-streaming'
 import { ChatTriggerType, TriggerPayload } from '../model'
-import { undefinedIfEmpty } from '../../../../shared'
+import { undefinedIfEmpty } from '../../../../shared/utilities/textUtilities'
 
 const fqnNameSizeDownLimit = 1
 const fqnNameSizeUpLimit = 256
diff --git a/packages/core/src/codewhispererChat/controllers/chat/controller.ts b/packages/core/src/codewhispererChat/controllers/chat/controller.ts
index a5205be78ca..e0ee9e0924b 100644
--- a/packages/core/src/codewhispererChat/controllers/chat/controller.ts
+++ b/packages/core/src/codewhispererChat/controllers/chat/controller.ts
@@ -49,11 +49,12 @@ import { CodeWhispererSettings } from '../../../codewhisperer/util/codewhisperer
 import { getSelectedCustomization } from '../../../codewhisperer/util/customizationUtil'
 import { getHttpStatusCode, AwsClientResponseError } from '../../../shared/errors'
 import { uiEventRecorder } from '../../../amazonq/util/eventRecorder'
-import { globals, waitUntil } from '../../../shared'
-import { telemetry } from '../../../shared/telemetry'
+import { telemetry } from '../../../shared/telemetry/telemetry'
 import { isSsoConnection } from '../../../auth/connection'
 import { inspect } from '../../../shared/utilities/collectionUtils'
 import { DefaultAmazonQAppInitContext } from '../../../amazonq/apps/initContext'
+import globals from '../../../shared/extensionGlobals'
+import { waitUntil } from '../../../shared/utilities/timeoutUtils'
 
 export interface ChatControllerMessagePublishers {
     readonly processPromptChatMessage: MessagePublisher<PromptMessage>
diff --git a/packages/core/src/codewhispererChat/controllers/chat/telemetryHelper.ts b/packages/core/src/codewhispererChat/controllers/chat/telemetryHelper.ts
index feaeec75969..3488d02d4f9 100644
--- a/packages/core/src/codewhispererChat/controllers/chat/telemetryHelper.ts
+++ b/packages/core/src/codewhispererChat/controllers/chat/telemetryHelper.ts
@@ -30,14 +30,14 @@ import {
 } from './model'
 import { TriggerEvent, TriggerEventsStorage } from '../../storages/triggerEvents'
 import globals from '../../../shared/extensionGlobals'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { codeWhispererClient } from '../../../codewhisperer/client/codewhisperer'
 import { isAwsError } from '../../../shared/errors'
 import { ChatMessageInteractionType } from '../../../codewhisperer/client/codewhispereruserclient'
 import { supportedLanguagesList } from '../chat/chatRequest/converter'
 import { AuthUtil } from '../../../codewhisperer/util/authUtil'
 import { getSelectedCustomization } from '../../../codewhisperer/util/customizationUtil'
-import { undefinedIfEmpty } from '../../../shared'
+import { undefinedIfEmpty } from '../../../shared/utilities/textUtilities'
 
 export function logSendTelemetryEventFailure(error: any) {
     let requestId: string | undefined
diff --git a/packages/core/src/codewhispererChat/controllers/chat/userIntent/userIntentRecognizer.ts b/packages/core/src/codewhispererChat/controllers/chat/userIntent/userIntentRecognizer.ts
index 32b6b274a51..4e3eabc0bc8 100644
--- a/packages/core/src/codewhispererChat/controllers/chat/userIntent/userIntentRecognizer.ts
+++ b/packages/core/src/codewhispererChat/controllers/chat/userIntent/userIntentRecognizer.ts
@@ -6,7 +6,7 @@
 import { UserIntent } from '@amzn/codewhisperer-streaming'
 import { EditorContextCommand } from '../../../commands/registerCommands'
 import { PromptMessage } from '../model'
-import { Auth } from '../../../../auth'
+import { Auth } from '../../../../auth/auth'
 
 export class UserIntentRecognizer {
     public getFromContextMenuCommand(command: EditorContextCommand): UserIntent | undefined {
diff --git a/packages/core/src/codewhispererChat/view/messages/messageListener.ts b/packages/core/src/codewhispererChat/view/messages/messageListener.ts
index 93c750ab01b..9c1dcb4b095 100644
--- a/packages/core/src/codewhispererChat/view/messages/messageListener.ts
+++ b/packages/core/src/codewhispererChat/view/messages/messageListener.ts
@@ -7,7 +7,7 @@ import { ExtensionMessage } from '../../../amazonq/webview/ui/commands'
 import { AuthController } from '../../../amazonq/auth/controller'
 import { ChatControllerMessagePublishers } from '../../controllers/chat/controller'
 import { ReferenceLogController } from './referenceLogController'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { openSettingsId } from '../../../shared/settings'
 
 export interface UIMessageListenerProps {
diff --git a/packages/core/src/commands.ts b/packages/core/src/commands.ts
index f1e77f24cf9..db038a72bbd 100644
--- a/packages/core/src/commands.ts
+++ b/packages/core/src/commands.ts
@@ -32,7 +32,7 @@ import {
     promptAndUseConnection,
 } from './auth/utils'
 import { showCodeWhispererConnectionPrompt } from './codewhisperer/util/showSsoPrompt'
-import { CommonAuthWebview } from './login/webview'
+import { CommonAuthWebview } from './login/webview/vue/backend'
 import { AuthSource, AuthSources } from './login/webview/util'
 import { ServiceItemId, isServiceItemId } from './login/webview/vue/types'
 import { authHelpUrl } from './shared/constants'
@@ -46,7 +46,7 @@ import { Commands, VsCodeCommandArg, placeholder, vscodeComponent } from './shar
 import { isValidResponse } from './shared/wizards/wizard'
 import { CancellationError } from './shared/utilities/timeoutUtils'
 import { ToolkitError } from './shared/errors'
-import { setContext } from './shared'
+import { setContext } from './shared/vscode/setContext'
 
 function switchConnections(auth: Auth | TreeNode | unknown) {
     if (!(auth instanceof Auth)) {
diff --git a/packages/core/src/dev/activation.ts b/packages/core/src/dev/activation.ts
index 0033eaa8548..e61295c502a 100644
--- a/packages/core/src/dev/activation.ts
+++ b/packages/core/src/dev/activation.ts
@@ -15,11 +15,11 @@ import { Wizard } from '../shared/wizards/wizard'
 import { deleteDevEnvCommand, installVsixCommand, openTerminalCommand } from './codecatalyst'
 import { isAnySsoConnection } from '../auth/connection'
 import { Auth } from '../auth/auth'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { entries } from '../shared/utilities/tsUtils'
 import { getEnvironmentSpecificMemento } from '../shared/utilities/mementos'
-import { setContext } from '../shared'
-import { telemetry } from '../shared/telemetry'
+import { setContext } from '../shared/vscode/setContext'
+import { telemetry } from '../shared/telemetry/telemetry'
 import { getSessionId } from '../shared/telemetry/util'
 import { NotificationsController } from '../notifications/controller'
 import { DevNotificationsState } from '../notifications/types'
diff --git a/packages/core/src/dev/beta.ts b/packages/core/src/dev/beta.ts
index 89bd085e84e..329907aa5a3 100644
--- a/packages/core/src/dev/beta.ts
+++ b/packages/core/src/dev/beta.ts
@@ -9,7 +9,7 @@ import * as vscode from 'vscode'
 import AdmZip from 'adm-zip'
 import got from 'got'
 import globals from '../shared/extensionGlobals'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import fs from '../shared/fs/fs'
 import { VSCODE_EXTENSION_ID } from '../shared/extensions'
 import { makeTemporaryToolkitFolder } from '../shared/filesystemUtilities'
diff --git a/packages/core/src/dev/codecatalyst.ts b/packages/core/src/dev/codecatalyst.ts
index 2c575f71eac..d9dd4e9e5a9 100644
--- a/packages/core/src/dev/codecatalyst.ts
+++ b/packages/core/src/dev/codecatalyst.ts
@@ -7,7 +7,7 @@ import { glob } from 'glob'
 import * as path from 'path'
 import * as vscode from 'vscode'
 import * as manifest from '../../package.json'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { selectCodeCatalystResource } from '../codecatalyst/wizards/selectResource'
 import { VSCODE_EXTENSION_ID } from '../shared/extensions'
 import { DevEnvironment, CodeCatalystClient } from '../shared/clients/codecatalystClient'
@@ -20,7 +20,7 @@ import { startVscodeRemote } from '../shared/extensions/ssh'
 import { isValidResponse } from '../shared/wizards/wizard'
 import { createQuickPick } from '../shared/ui/pickerPrompter'
 import { createCommonButtons } from '../shared/ui/buttons'
-import { fs } from '../shared'
+import { fs } from '../shared/fs/fs'
 
 type LazyProgress<T> = vscode.Progress<T> & vscode.Disposable & { getToken(): Timeout }
 
diff --git a/packages/core/src/docdb/activation.ts b/packages/core/src/docdb/activation.ts
index 23ee206e4f6..62b61d5e490 100644
--- a/packages/core/src/docdb/activation.ts
+++ b/packages/core/src/docdb/activation.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { Commands } from '../shared'
+import { Commands } from '../shared/vscode/commands2'
 import { ExtContext } from '../shared/extensions'
 import { DBResourceNode } from './explorer/dbResourceNode'
 import { DocumentDBNode } from './explorer/docdbNode'
@@ -23,7 +23,7 @@ import { renameInstance } from './commands/renameInstance'
 import { addTag, listTags, removeTag } from './commands/tagCommands'
 import { Uri } from 'vscode'
 import { openUrl } from '../shared/utilities/vsCodeUtils'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 
 /**
  * A utility function to automatically invoke trackChanges after a command.
diff --git a/packages/core/src/docdb/commands/addRegion.ts b/packages/core/src/docdb/commands/addRegion.ts
index 403778e6c6a..ab3e6d1b721 100644
--- a/packages/core/src/docdb/commands/addRegion.ts
+++ b/packages/core/src/docdb/commands/addRegion.ts
@@ -4,13 +4,13 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../shared/logger'
-import { telemetry } from '../../shared/telemetry'
+import { getLogger } from '../../shared/logger/logger'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { localize } from '../../shared/utilities/vsCodeUtils'
 import { DBClusterNode } from '../explorer/dbClusterNode'
 import { DBGlobalClusterNode } from '../explorer/dbGlobalClusterNode'
 import { DefaultDocumentDBClient } from '../../shared/clients/docdbClient'
-import { ToolkitError } from '../../shared'
+import { ToolkitError } from '../../shared/errors'
 import { showViewLogsMessage } from '../../shared/utilities/messages'
 import { isValidResponse } from '../../shared/wizards/wizard'
 import { CancellationError } from '../../shared/utilities/timeoutUtils'
diff --git a/packages/core/src/docdb/commands/createCluster.ts b/packages/core/src/docdb/commands/createCluster.ts
index 8d0b9658fc0..62689319158 100644
--- a/packages/core/src/docdb/commands/createCluster.ts
+++ b/packages/core/src/docdb/commands/createCluster.ts
@@ -4,8 +4,9 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger, ToolkitError } from '../../shared'
-import { telemetry } from '../../shared/telemetry'
+import { ToolkitError } from '../../shared/errors'
+import { getLogger } from '../../shared/logger/logger'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { localize } from '../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage } from '../../shared/utilities/messages'
 import { DocumentDBNode } from '../explorer/docdbNode'
diff --git a/packages/core/src/docdb/commands/createInstance.ts b/packages/core/src/docdb/commands/createInstance.ts
index 2387bdecd84..34e7808ce62 100644
--- a/packages/core/src/docdb/commands/createInstance.ts
+++ b/packages/core/src/docdb/commands/createInstance.ts
@@ -4,8 +4,9 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger, ToolkitError } from '../../shared'
-import { telemetry } from '../../shared/telemetry'
+import { ToolkitError } from '../../shared/errors'
+import { getLogger } from '../../shared/logger/logger'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { localize } from '../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage } from '../../shared/utilities/messages'
 import { DBClusterNode } from '../explorer/dbClusterNode'
diff --git a/packages/core/src/docdb/commands/deleteCluster.ts b/packages/core/src/docdb/commands/deleteCluster.ts
index 6b538cb8d00..bb725ae2ab1 100644
--- a/packages/core/src/docdb/commands/deleteCluster.ts
+++ b/packages/core/src/docdb/commands/deleteCluster.ts
@@ -4,13 +4,14 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger, ToolkitError } from '../../shared'
+import { ToolkitError } from '../../shared/errors'
+import { getLogger } from '../../shared/logger/logger'
 import { localize } from '../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage } from '../../shared/utilities/messages'
 import { DBClusterNode } from '../explorer/dbClusterNode'
 import { showQuickPick } from '../../shared/ui/pickerPrompter'
 import { formatDate, formatTime } from '../../shared/date'
-import { telemetry } from '../../shared/telemetry'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { DBElasticClusterNode } from '../explorer/dbElasticClusterNode'
 import { assertNodeAvailable } from '../utils'
 
diff --git a/packages/core/src/docdb/commands/deleteInstance.ts b/packages/core/src/docdb/commands/deleteInstance.ts
index 580d50c801c..6202d317a07 100644
--- a/packages/core/src/docdb/commands/deleteInstance.ts
+++ b/packages/core/src/docdb/commands/deleteInstance.ts
@@ -4,12 +4,13 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger, ToolkitError } from '../../shared'
+import { ToolkitError } from '../../shared/errors'
+import { getLogger } from '../../shared/logger/logger'
 import { localize } from '../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage } from '../../shared/utilities/messages'
 import { DBInstanceNode } from '../explorer/dbInstanceNode'
 import { DBClusterNode } from '../explorer/dbClusterNode'
-import { telemetry } from '../../shared/telemetry'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { assertNodeAvailable } from '../utils'
 
 /**
diff --git a/packages/core/src/docdb/commands/modifyInstance.ts b/packages/core/src/docdb/commands/modifyInstance.ts
index 626c1be3d97..3df5febaf45 100644
--- a/packages/core/src/docdb/commands/modifyInstance.ts
+++ b/packages/core/src/docdb/commands/modifyInstance.ts
@@ -4,7 +4,8 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger, ToolkitError } from '../../shared'
+import { ToolkitError } from '../../shared/errors'
+import { getLogger } from '../../shared/logger/logger'
 import { localize } from '../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage } from '../../shared/utilities/messages'
 import { DBInstanceNode } from '../explorer/dbInstanceNode'
@@ -12,7 +13,7 @@ import { DBCluster, ModifyDBInstanceMessage } from '@aws-sdk/client-docdb'
 import { DBStorageType, DocumentDBClient } from '../../shared/clients/docdbClient'
 import { createQuickPick, DataQuickPickItem } from '../../shared/ui/pickerPrompter'
 import { isValidResponse } from '../../shared/wizards/wizard'
-import { telemetry } from '../../shared/telemetry'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { assertNodeAvailable } from '../utils'
 
 /**
diff --git a/packages/core/src/docdb/commands/rebootInstance.ts b/packages/core/src/docdb/commands/rebootInstance.ts
index 43458f4c9a6..ab706803d87 100644
--- a/packages/core/src/docdb/commands/rebootInstance.ts
+++ b/packages/core/src/docdb/commands/rebootInstance.ts
@@ -5,11 +5,12 @@
 
 import * as vscode from 'vscode'
 import * as localizedText from '../../shared/localizedText'
-import { getLogger, ToolkitError } from '../../shared'
+import { ToolkitError } from '../../shared/errors'
+import { getLogger } from '../../shared/logger/logger'
 import { CancellationError } from '../../shared/utilities/timeoutUtils'
 import { localize } from '../../shared/utilities/vsCodeUtils'
 import { showConfirmationMessage, showViewLogsMessage } from '../../shared/utilities/messages'
-import { telemetry } from '../../shared/telemetry'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { DBInstanceNode } from '../explorer/dbInstanceNode'
 import { assertNodeAvailable } from '../utils'
 
diff --git a/packages/core/src/docdb/commands/renameCluster.ts b/packages/core/src/docdb/commands/renameCluster.ts
index f4067983f6a..f64ae7b1d98 100644
--- a/packages/core/src/docdb/commands/renameCluster.ts
+++ b/packages/core/src/docdb/commands/renameCluster.ts
@@ -4,13 +4,15 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger, sleep, ToolkitError } from '../../shared'
+import { ToolkitError } from '../../shared/errors'
+import { getLogger } from '../../shared/logger/logger'
 import { localize } from '../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage } from '../../shared/utilities/messages'
 import { assertNodeAvailable, validateClusterName } from '../utils'
 import { DBClusterNode } from '../explorer/dbClusterNode'
 import { DBGlobalClusterNode } from '../explorer/dbGlobalClusterNode'
-import { telemetry } from '../../shared/telemetry'
+import { telemetry } from '../../shared/telemetry/telemetry'
+import { sleep } from '../../shared/utilities/timeoutUtils'
 
 /**
  * Renames a DocumentDB cluster.
diff --git a/packages/core/src/docdb/commands/renameInstance.ts b/packages/core/src/docdb/commands/renameInstance.ts
index e7b26131eb7..414f780e521 100644
--- a/packages/core/src/docdb/commands/renameInstance.ts
+++ b/packages/core/src/docdb/commands/renameInstance.ts
@@ -4,12 +4,13 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger, ToolkitError } from '../../shared'
+import { getLogger } from '../../shared/logger/logger'
+import { ToolkitError } from '../../shared/errors'
 import { localize } from '../../shared/utilities/vsCodeUtils'
 import { showViewLogsMessage } from '../../shared/utilities/messages'
 import { assertNodeAvailable, validateInstanceName } from '../utils'
 import { DBInstanceNode } from '../explorer/dbInstanceNode'
-import { telemetry } from '../../shared/telemetry'
+import { telemetry } from '../../shared/telemetry/telemetry'
 
 /**
  * Renames a DocumentDB instance.
diff --git a/packages/core/src/docdb/commands/startCluster.ts b/packages/core/src/docdb/commands/startCluster.ts
index a1ef83ab7be..60dbda80e70 100644
--- a/packages/core/src/docdb/commands/startCluster.ts
+++ b/packages/core/src/docdb/commands/startCluster.ts
@@ -4,8 +4,8 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../shared/logger'
-import { telemetry } from '../../shared/telemetry'
+import { getLogger } from '../../shared/logger/logger'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { localize } from '../../shared/utilities/vsCodeUtils'
 import { DBClusterNode } from '../explorer/dbClusterNode'
 
diff --git a/packages/core/src/docdb/commands/stopCluster.ts b/packages/core/src/docdb/commands/stopCluster.ts
index e642a78b58a..46f23f3eab9 100644
--- a/packages/core/src/docdb/commands/stopCluster.ts
+++ b/packages/core/src/docdb/commands/stopCluster.ts
@@ -5,8 +5,8 @@
 
 import * as vscode from 'vscode'
 import * as localizedText from '../../shared/localizedText'
-import { getLogger } from '../../shared/logger'
-import { telemetry } from '../../shared/telemetry'
+import { getLogger } from '../../shared/logger/logger'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { localize } from '../../shared/utilities/vsCodeUtils'
 import { CancellationError } from '../../shared/utilities/timeoutUtils'
 import { showConfirmationMessage } from '../../shared/utilities/messages'
diff --git a/packages/core/src/docdb/commands/tagCommands.ts b/packages/core/src/docdb/commands/tagCommands.ts
index 6265451381c..d3c46176adb 100644
--- a/packages/core/src/docdb/commands/tagCommands.ts
+++ b/packages/core/src/docdb/commands/tagCommands.ts
@@ -4,12 +4,12 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../shared/logger'
-import { telemetry } from '../../shared/telemetry'
+import { getLogger } from '../../shared/logger/logger'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { localize } from '../../shared/utilities/vsCodeUtils'
 import { DBResourceNode } from '../explorer/dbResourceNode'
 import { DataQuickPickItem, showQuickPick } from '../../shared/ui/pickerPrompter'
-import { ToolkitError } from '../../shared'
+import { ToolkitError } from '../../shared/errors'
 
 export async function listTags(node: DBResourceNode): Promise<void> {
     return telemetry.docdb_listTags.run(async () => {
diff --git a/packages/core/src/docdb/explorer/dbClusterNode.ts b/packages/core/src/docdb/explorer/dbClusterNode.ts
index f611d023120..5544523d6f9 100644
--- a/packages/core/src/docdb/explorer/dbClusterNode.ts
+++ b/packages/core/src/docdb/explorer/dbClusterNode.ts
@@ -9,7 +9,7 @@ import { inspect } from 'util'
 import { copyToClipboard } from '../../shared/utilities/messages'
 import { makeChildrenNodes } from '../../shared/treeview/utils'
 import { localize } from '../../shared/utilities/vsCodeUtils'
-import { telemetry } from '../../shared/telemetry'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { CreateDBInstanceMessage, DBCluster, ModifyDBClusterMessage } from '@aws-sdk/client-docdb'
 import { AWSTreeNodeBase } from '../../shared/treeview/nodes/awsTreeNodeBase'
 import { DBResourceNode } from './dbResourceNode'
@@ -17,9 +17,9 @@ import { DBInstanceNode } from './dbInstanceNode'
 import { PlaceholderNode } from '../../shared/treeview/nodes/placeholderNode'
 import { DBInstance, DocumentDBClient } from '../../shared/clients/docdbClient'
 import { DocDBContext } from './docdbContext'
-import { toTitleCase } from '../../shared'
+import { toTitleCase } from '../../shared/utilities/textUtilities'
 import { getAwsConsoleUrl } from '../../shared/awsConsole'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 
 export type DBClusterRole = 'global' | 'regional' | 'primary' | 'secondary'
 
diff --git a/packages/core/src/docdb/explorer/dbElasticClusterNode.ts b/packages/core/src/docdb/explorer/dbElasticClusterNode.ts
index 9534c405f63..d228c3bbefd 100644
--- a/packages/core/src/docdb/explorer/dbElasticClusterNode.ts
+++ b/packages/core/src/docdb/explorer/dbElasticClusterNode.ts
@@ -12,7 +12,7 @@ import { DocDBContext } from './docdbContext'
 import { copyToClipboard } from '../../shared/utilities/messages'
 import { localize } from '../../shared/utilities/vsCodeUtils'
 import { getAwsConsoleUrl } from '../../shared/awsConsole'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 
 /**
  * An AWS Explorer node representing DocumentDB elastic clusters.
diff --git a/packages/core/src/docdb/explorer/dbGlobalClusterNode.ts b/packages/core/src/docdb/explorer/dbGlobalClusterNode.ts
index fcebe18e3f8..7ab15e01a15 100644
--- a/packages/core/src/docdb/explorer/dbGlobalClusterNode.ts
+++ b/packages/core/src/docdb/explorer/dbGlobalClusterNode.ts
@@ -7,7 +7,7 @@ import * as vscode from 'vscode'
 import { inspect } from 'util'
 import { makeChildrenNodes } from '../../shared/treeview/utils'
 import { localize } from '../../shared/utilities/vsCodeUtils'
-import { telemetry } from '../../shared/telemetry'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { AWSTreeNodeBase } from '../../shared/treeview/nodes/awsTreeNodeBase'
 import { PlaceholderNode } from '../../shared/treeview/nodes/placeholderNode'
 import { DBClusterNode, DBClusterRole } from './dbClusterNode'
@@ -17,7 +17,7 @@ import { DBResourceNode } from './dbResourceNode'
 import { DocDBContext } from './docdbContext'
 import { copyToClipboard } from '../../shared/utilities/messages'
 import { getAwsConsoleUrl } from '../../shared/awsConsole'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 
 function getRegionFromArn(arn: string) {
     const match = arn.match(/:rds:([^:]+):.*:cluster:/)
diff --git a/packages/core/src/docdb/explorer/dbInstanceNode.ts b/packages/core/src/docdb/explorer/dbInstanceNode.ts
index 041640ce562..3a839971e08 100644
--- a/packages/core/src/docdb/explorer/dbInstanceNode.ts
+++ b/packages/core/src/docdb/explorer/dbInstanceNode.ts
@@ -11,9 +11,9 @@ import { DBResourceNode } from './dbResourceNode'
 import { DBClusterNode } from './dbClusterNode'
 import { ModifyDBInstanceMessage } from '@aws-sdk/client-docdb'
 import { copyToClipboard } from '../../shared/utilities/messages'
-import { toTitleCase } from '../../shared'
 import { getAwsConsoleUrl } from '../../shared/awsConsole'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
+import { toTitleCase } from '../../shared/utilities/textUtilities'
 
 /**
  * An AWS Explorer node representing a DocumentDB instance.
diff --git a/packages/core/src/docdb/explorer/dbResourceNode.ts b/packages/core/src/docdb/explorer/dbResourceNode.ts
index a9ded2bea70..259a867024c 100644
--- a/packages/core/src/docdb/explorer/dbResourceNode.ts
+++ b/packages/core/src/docdb/explorer/dbResourceNode.ts
@@ -8,8 +8,8 @@ import { inspect } from 'util'
 import { AWSResourceNode } from '../../shared/treeview/nodes/awsResourceNode'
 import { AWSTreeNodeBase } from '../../shared/treeview/nodes/awsTreeNodeBase'
 import { DocumentDBClient } from '../../shared/clients/docdbClient'
-import { waitUntil } from '../../shared'
-import { getLogger } from '../../shared/logger'
+import { waitUntil } from '../../shared/utilities/timeoutUtils'
+import { getLogger } from '../../shared/logger/logger'
 import { PollingSet } from '../../shared/utilities/pollingSet'
 
 /** An AWS Explorer node representing a DocumentDB resource. */
diff --git a/packages/core/src/docdb/explorer/docdbNode.ts b/packages/core/src/docdb/explorer/docdbNode.ts
index 18ebed2d0e1..e94e7c41152 100644
--- a/packages/core/src/docdb/explorer/docdbNode.ts
+++ b/packages/core/src/docdb/explorer/docdbNode.ts
@@ -12,10 +12,10 @@ import { makeChildrenNodes } from '../../shared/treeview/utils'
 import { DBElasticCluster, DocumentDBClient } from '../../shared/clients/docdbClient'
 import { DBClusterNode } from './dbClusterNode'
 import { DBElasticClusterNode } from './dbElasticClusterNode'
-import { telemetry } from '../../shared/telemetry'
+import { telemetry } from '../../shared/telemetry/telemetry'
 import { DBGlobalClusterNode } from './dbGlobalClusterNode'
 import { DBCluster } from '@aws-sdk/client-docdb'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { DBResourceNode } from './dbResourceNode'
 
 /**
diff --git a/packages/core/src/docdb/utils.ts b/packages/core/src/docdb/utils.ts
index 44e90089c41..09b71d9fdf9 100644
--- a/packages/core/src/docdb/utils.ts
+++ b/packages/core/src/docdb/utils.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { ToolkitError } from '../shared'
+import { ToolkitError } from '../shared/errors'
 import { localize } from '../shared/utilities/vsCodeUtils'
 import { DBInstanceNode } from './explorer/dbInstanceNode'
 import { DBResourceNode } from './explorer/dbResourceNode'
diff --git a/packages/core/src/docdb/wizards/createGlobalClusterWizard.ts b/packages/core/src/docdb/wizards/createGlobalClusterWizard.ts
index e177047fcb4..de88522dff4 100644
--- a/packages/core/src/docdb/wizards/createGlobalClusterWizard.ts
+++ b/packages/core/src/docdb/wizards/createGlobalClusterWizard.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { globals } from '../../shared'
+import globals from '../../shared/extensionGlobals'
 import { DocDBEngine, DocumentDBClient } from '../../shared/clients/docdbClient'
 import { createExitPrompter } from '../../shared/ui/common/exitPrompter'
 import { createRegionPrompter } from '../../shared/ui/common/region'
diff --git a/packages/core/src/docdb/wizards/elasticClusterWizard.ts b/packages/core/src/docdb/wizards/elasticClusterWizard.ts
index 4dca7c99b51..b28d2f20751 100644
--- a/packages/core/src/docdb/wizards/elasticClusterWizard.ts
+++ b/packages/core/src/docdb/wizards/elasticClusterWizard.ts
@@ -11,7 +11,7 @@ import { createInputBox } from '../../shared/ui/inputPrompter'
 import { DataQuickPickItem, createQuickPick } from '../../shared/ui/pickerPrompter'
 import { createCommonButtons } from '../../shared/ui/buttons'
 import { Auth, CreateClusterInput } from '@aws-sdk/client-docdb-elastic'
-import { Prompter } from '../../shared'
+import { Prompter } from '../../shared/ui/prompter'
 
 const DocDBElasticHelpUrl = 'https://docs.aws.amazon.com/documentdb/latest/developerguide/elastic-how-it-works.html'
 const DefaultShardCount = 2
diff --git a/packages/core/src/dynamicResources/awsResourceManager.ts b/packages/core/src/dynamicResources/awsResourceManager.ts
index de990e6c6b9..76a45996f28 100644
--- a/packages/core/src/dynamicResources/awsResourceManager.ts
+++ b/packages/core/src/dynamicResources/awsResourceManager.ts
@@ -18,7 +18,7 @@ import { getTabSizeSetting } from '../shared/utilities/editorUtilities'
 import { ResourceNode } from './explorer/nodes/resourceNode'
 import { ResourceTypeNode } from './explorer/nodes/resourceTypeNode'
 import globals from '../shared/extensionGlobals'
-import { fs } from '../shared'
+import { fs } from '../shared/fs/fs'
 
 export const resourceFileGlobPattern = '**/*.awsResource.json'
 
diff --git a/packages/core/src/dynamicResources/explorer/nodes/resourceTypeNode.ts b/packages/core/src/dynamicResources/explorer/nodes/resourceTypeNode.ts
index c2ada853dbd..7f3ffc6aaf1 100644
--- a/packages/core/src/dynamicResources/explorer/nodes/resourceTypeNode.ts
+++ b/packages/core/src/dynamicResources/explorer/nodes/resourceTypeNode.ts
@@ -6,7 +6,7 @@
 import * as vscode from 'vscode'
 import { ChildNodeLoader, ChildNodePage } from '../../../awsexplorer/childNodeLoader'
 import { CloudControlClient } from '../../../shared/clients/cloudControlClient'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { AWSTreeNodeBase } from '../../../shared/treeview/nodes/awsTreeNodeBase'
 import { LoadMoreNode } from '../../../shared/treeview/nodes/loadMoreNode'
 import { PlaceholderNode } from '../../../shared/treeview/nodes/placeholderNode'
diff --git a/packages/core/src/eventSchemas/commands/downloadSchemaItemCode.ts b/packages/core/src/eventSchemas/commands/downloadSchemaItemCode.ts
index 6c6ec818444..b89a128ba96 100644
--- a/packages/core/src/eventSchemas/commands/downloadSchemaItemCode.ts
+++ b/packages/core/src/eventSchemas/commands/downloadSchemaItemCode.ts
@@ -12,7 +12,7 @@ import * as vscode from 'vscode'
 import { SchemaClient } from '../../shared/clients/schemaClient'
 import { makeTemporaryToolkitFolder, tryRemoveFolder } from '../../shared/filesystemUtilities'
 import * as localizedText from '../../shared/localizedText'
-import { getLogger, Logger } from '../../shared/logger'
+import { getLogger, Logger } from '../../shared/logger/logger'
 import { Result } from '../../shared/telemetry/telemetry'
 import { SchemaItemNode } from '../explorer/schemaItemNode'
 import { getLanguageDetails } from '../models/schemaCodeLangs'
diff --git a/packages/core/src/eventSchemas/commands/viewSchemaItem.ts b/packages/core/src/eventSchemas/commands/viewSchemaItem.ts
index f3eca0428e5..cc40911ea98 100644
--- a/packages/core/src/eventSchemas/commands/viewSchemaItem.ts
+++ b/packages/core/src/eventSchemas/commands/viewSchemaItem.ts
@@ -7,7 +7,7 @@ import * as nls from 'vscode-nls'
 const localize = nls.loadMessageBundle()
 
 import * as vscode from 'vscode'
-import { getLogger, Logger } from '../../shared/logger'
+import { getLogger, Logger } from '../../shared/logger/logger'
 import { Result } from '../../shared/telemetry/telemetry'
 import { getTabSizeSetting } from '../../shared/utilities/editorUtilities'
 import { SchemaItemNode } from '../explorer/schemaItemNode'
diff --git a/packages/core/src/eventSchemas/providers/schemasDataProvider.ts b/packages/core/src/eventSchemas/providers/schemasDataProvider.ts
index ec280238183..2df9469d8cb 100644
--- a/packages/core/src/eventSchemas/providers/schemasDataProvider.ts
+++ b/packages/core/src/eventSchemas/providers/schemasDataProvider.ts
@@ -6,7 +6,7 @@
 import * as AWS from '@aws-sdk/types'
 import { Schemas } from 'aws-sdk'
 import { SchemaClient } from '../../shared/clients/schemaClient'
-import { getLogger, Logger } from '../../shared/logger'
+import { getLogger, Logger } from '../../shared/logger/logger'
 import { toArrayAsync } from '../../shared/utilities/collectionUtils'
 
 export class Cache {
diff --git a/packages/core/src/eventSchemas/vue/searchSchemas.ts b/packages/core/src/eventSchemas/vue/searchSchemas.ts
index a5dcb55527d..37efc145753 100644
--- a/packages/core/src/eventSchemas/vue/searchSchemas.ts
+++ b/packages/core/src/eventSchemas/vue/searchSchemas.ts
@@ -14,7 +14,7 @@ import { SchemasNode } from '../explorer/schemasNode'
 import { listRegistryItems, searchSchemas } from '../utils'
 import { DefaultSchemaClient, SchemaClient } from '../../shared/clients/schemaClient'
 
-import { getLogger, Logger } from '../../shared/logger'
+import { getLogger, Logger } from '../../shared/logger/logger'
 import { Result } from '../../shared/telemetry/telemetry'
 import { toArrayAsync } from '../../shared/utilities/collectionUtils'
 import { getTabSizeSetting } from '../../shared/utilities/editorUtilities'
diff --git a/packages/core/src/extension.ts b/packages/core/src/extension.ts
index 4a57f96e8fe..27bdd869b1e 100644
--- a/packages/core/src/extension.ts
+++ b/packages/core/src/extension.ts
@@ -49,8 +49,10 @@ import { registerCommands } from './commands'
 // In web mode everything must be in a single file, so things like the endpoints file will not be available.
 // The following imports the endpoints file, which causes webpack to bundle it in the final output file
 import endpoints from '../resources/endpoints.json'
-import { getLogger, maybeShowMinVscodeWarning, setupUninstallHandler } from './shared'
 import { showViewLogsMessage } from './shared/utilities/messages'
+import { setupUninstallHandler } from './shared/handleUninstall'
+import { maybeShowMinVscodeWarning } from './shared/extensionStartup'
+import { getLogger } from './shared/logger/logger'
 
 disableAwsSdkWarning()
 
diff --git a/packages/core/src/extensionNode.ts b/packages/core/src/extensionNode.ts
index e2e63614381..a3e5e03b4ab 100644
--- a/packages/core/src/extensionNode.ts
+++ b/packages/core/src/extensionNode.ts
@@ -46,6 +46,7 @@ import globals from './shared/extensionGlobals'
 import { Experiments, Settings, showSettingsFailedMsg } from './shared/settings'
 import { isReleaseVersion } from './shared/vscode/env'
 import { AuthStatus, AuthUserState, telemetry } from './shared/telemetry/telemetry'
+import { ExtStartUpSources } from './shared/telemetry/util'
 import { Auth } from './auth/auth'
 import { getTelemetryMetadataForConn } from './auth/connection'
 import { registerSubmitFeedback } from './feedback/vue/submitFeedback'
@@ -53,12 +54,13 @@ import { activateCommon, deactivateCommon } from './extension'
 import { learnMoreAmazonQCommand, qExtensionPageCommand, dismissQTree } from './amazonq/explorer/amazonQChildrenNodes'
 import { codeWhispererCoreScopes } from './codewhisperer/util/authUtil'
 import { installAmazonQExtension } from './codewhisperer/commands/basicCommands'
-import { isExtensionInstalled, VSCODE_EXTENSION_ID } from './shared/utilities'
+import { VSCODE_EXTENSION_ID } from './shared/extensions'
+import { isExtensionInstalled } from './shared/utilities/vsCodeUtils'
 import { ExtensionUse, getAuthFormIdsFromConnection, initializeCredentialsProviderManager } from './auth/utils'
-import { ExtStartUpSources } from './shared/telemetry'
 import { activate as activateThreatComposerEditor } from './threatComposer/activation'
 import { isSsoConnection, hasScopes } from './auth/connection'
-import { CrashMonitoring, setContext } from './shared'
+import { CrashMonitoring } from './shared/crashMonitoring'
+import { setContext } from './shared/vscode/setContext'
 import { AuthFormId } from './login/webview/vue/types'
 
 let localize: nls.LocalizeFunc
diff --git a/packages/core/src/extensionWeb.ts b/packages/core/src/extensionWeb.ts
index 9c274f559b6..01fa0f667db 100644
--- a/packages/core/src/extensionWeb.ts
+++ b/packages/core/src/extensionWeb.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from './shared/logger'
+import { getLogger } from './shared/logger/logger'
 import { activateCommon, deactivateCommon } from './extension'
 import { activateWebShared } from './extensionWebShared'
 
diff --git a/packages/core/src/extensionWebShared.ts b/packages/core/src/extensionWebShared.ts
index af14c87696c..1a62ab723a4 100644
--- a/packages/core/src/extensionWebShared.ts
+++ b/packages/core/src/extensionWebShared.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from './shared/logger'
+import { getLogger } from './shared/logger/logger'
 import os from 'os'
 
 /**
diff --git a/packages/core/src/feedback/vue/submitFeedback.ts b/packages/core/src/feedback/vue/submitFeedback.ts
index 838030a4b88..2bbfc39d66c 100644
--- a/packages/core/src/feedback/vue/submitFeedback.ts
+++ b/packages/core/src/feedback/vue/submitFeedback.ts
@@ -4,7 +4,7 @@
  */
 
 import globals from '../../shared/extensionGlobals'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import * as vscode from 'vscode'
 import { TelemetryService } from '../../shared/telemetry/telemetryService'
 import { localize } from '../../shared/utilities/vsCodeUtils'
diff --git a/packages/core/src/lambda/activation.ts b/packages/core/src/lambda/activation.ts
index 2b160e89bdf..d799173697e 100644
--- a/packages/core/src/lambda/activation.ts
+++ b/packages/core/src/lambda/activation.ts
@@ -22,7 +22,7 @@ import { getSourceNode } from '../shared/utilities/treeNodeUtils'
 import { tailLogGroup } from '../awsService/cloudWatchLogs/commands/tailLogGroup'
 import { liveTailRegistry, liveTailCodeLensProvider } from '../awsService/cloudWatchLogs/activation'
 import { getFunctionLogGroupName } from '../awsService/cloudWatchLogs/activation'
-import { ToolkitError, isError } from '../shared'
+import { ToolkitError, isError } from '../shared/errors'
 import { LogStreamFilterResponse } from '../awsService/cloudWatchLogs/wizard/liveTailLogStreamSubmenu'
 
 /**
diff --git a/packages/core/src/lambda/commands/createNewSamApp.ts b/packages/core/src/lambda/commands/createNewSamApp.ts
index 8c6f5fbab19..c53edf2518b 100644
--- a/packages/core/src/lambda/commands/createNewSamApp.ts
+++ b/packages/core/src/lambda/commands/createNewSamApp.ts
@@ -22,7 +22,7 @@ import { ActivationReloadState, SamInitState } from '../../shared/activationRelo
 import { AwsContext } from '../../shared/awsContext'
 
 import { fileExists, isInDirectory, readFileAsString } from '../../shared/filesystemUtilities'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { RegionProvider } from '../../shared/regions/regionProvider'
 import { getSamCliVersion, getSamCliContext, SamCliContext } from '../../shared/sam/cli/samCliContext'
 import { runSamCliInit, SamCliInitArgs } from '../../shared/sam/cli/samCliInit'
@@ -46,7 +46,7 @@ import { telemetry } from '../../shared/telemetry/telemetry'
 import { LambdaArchitecture, Result, Runtime } from '../../shared/telemetry/telemetry'
 import { getTelemetryReason, getTelemetryResult } from '../../shared/errors'
 import { openUrl, replaceVscodeVars } from '../../shared/utilities/vsCodeUtils'
-import { fs } from '../../shared'
+import { fs } from '../../shared/fs/fs'
 import { ChildProcess } from '../../shared/utilities/processUtils'
 
 export const samInitTemplateFiles: string[] = ['template.yaml', 'template.yml']
diff --git a/packages/core/src/lambda/commands/deleteCloudFormation.ts b/packages/core/src/lambda/commands/deleteCloudFormation.ts
index 57e61a2361d..67c903f35c3 100644
--- a/packages/core/src/lambda/commands/deleteCloudFormation.ts
+++ b/packages/core/src/lambda/commands/deleteCloudFormation.ts
@@ -10,7 +10,7 @@ import * as vscode from 'vscode'
 import { DefaultCloudFormationClient } from '../../shared/clients/cloudFormationClient'
 
 import * as localizedText from '../../shared/localizedText'
-import { getLogger, Logger } from '../../shared/logger'
+import { getLogger, Logger } from '../../shared/logger/logger'
 import { Result } from '../../shared/telemetry/telemetry'
 import { CloudFormationStackNode } from '../explorer/cloudFormationNodes'
 import { showConfirmationMessage } from '../../shared/utilities/messages'
diff --git a/packages/core/src/lambda/commands/downloadLambda.ts b/packages/core/src/lambda/commands/downloadLambda.ts
index 815ff2576e9..e2e1dc2be91 100644
--- a/packages/core/src/lambda/commands/downloadLambda.ts
+++ b/packages/core/src/lambda/commands/downloadLambda.ts
@@ -13,7 +13,7 @@ import { LaunchConfiguration, getReferencedHandlerPaths } from '../../shared/deb
 
 import { makeTemporaryToolkitFolder, fileExists, tryRemoveFolder } from '../../shared/filesystemUtilities'
 import * as localizedText from '../../shared/localizedText'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { HttpResourceFetcher } from '../../shared/resourcefetcher/node/httpResourceFetcher'
 import { createCodeAwsSamDebugConfig } from '../../shared/sam/debugger/awsSamDebugConfiguration'
 import * as pathutils from '../../shared/utilities/pathUtils'
@@ -25,7 +25,7 @@ import { Progress } from 'got/dist/source'
 import { DefaultLambdaClient } from '../../shared/clients/lambdaClient'
 import { telemetry } from '../../shared/telemetry/telemetry'
 import { Result, Runtime } from '../../shared/telemetry/telemetry'
-import { fs } from '../../shared'
+import { fs } from '../../shared/fs/fs'
 
 export async function downloadLambdaCommand(functionNode: LambdaFunctionNode) {
     const result = await runDownloadLambda(functionNode)
diff --git a/packages/core/src/lambda/commands/listSamResources.ts b/packages/core/src/lambda/commands/listSamResources.ts
index 5a0d1678c9b..80d13a1c71b 100644
--- a/packages/core/src/lambda/commands/listSamResources.ts
+++ b/packages/core/src/lambda/commands/listSamResources.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { runSamCliListResource } from '../../shared/sam/cli/samCliListResources'
 
 export interface StackResource {
diff --git a/packages/core/src/lambda/commands/uploadLambda.ts b/packages/core/src/lambda/commands/uploadLambda.ts
index e5a4ce34755..692d07409a2 100644
--- a/packages/core/src/lambda/commands/uploadLambda.ts
+++ b/packages/core/src/lambda/commands/uploadLambda.ts
@@ -10,11 +10,11 @@ const localize = nls.loadMessageBundle()
 
 import AdmZip from 'adm-zip'
 import * as path from 'path'
-import { fs } from '../../shared'
+import { fs } from '../../shared/fs/fs'
 import { showConfirmationMessage, showViewLogsMessage } from '../../shared/utilities/messages'
 import { makeTemporaryToolkitFolder, tryRemoveFolder } from '../../shared/filesystemUtilities'
 import * as localizedText from '../../shared/localizedText'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { SamCliBuildInvocation } from '../../shared/sam/cli/samCliBuild'
 import { getSamCliContext } from '../../shared/sam/cli/samCliContext'
 import { SamTemplateGenerator } from '../../shared/templates/sam/samTemplateGenerator'
diff --git a/packages/core/src/lambda/config/configureParameterOverrides.ts b/packages/core/src/lambda/config/configureParameterOverrides.ts
index 39da13b37c2..70e9d1936d8 100644
--- a/packages/core/src/lambda/config/configureParameterOverrides.ts
+++ b/packages/core/src/lambda/config/configureParameterOverrides.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { getNormalizedRelativePath } from '../../shared/utilities/pathUtils'
 import { getChildrenRange } from '../../shared/utilities/symbolUtilities'
 import { getTabSize } from '../../shared/utilities/textDocumentUtilities'
diff --git a/packages/core/src/lambda/config/samParameterCompletionItemProvider.ts b/packages/core/src/lambda/config/samParameterCompletionItemProvider.ts
index 9fede2897c5..f408733f886 100644
--- a/packages/core/src/lambda/config/samParameterCompletionItemProvider.ts
+++ b/packages/core/src/lambda/config/samParameterCompletionItemProvider.ts
@@ -6,7 +6,7 @@
 import * as path from 'path'
 import * as vscode from 'vscode'
 import * as CloudFormation from '../../shared/cloudformation/cloudformation'
-import { getLogger, Logger } from '../../shared/logger'
+import { getLogger, Logger } from '../../shared/logger/logger'
 import { getChildrenRange, loadSymbols, LoadSymbolsContext } from '../../shared/utilities/symbolUtilities'
 import { getParameterNames } from '../config/parameterUtils'
 
diff --git a/packages/core/src/lambda/config/templates.ts b/packages/core/src/lambda/config/templates.ts
index 5077551bacf..52beae0e953 100644
--- a/packages/core/src/lambda/config/templates.ts
+++ b/packages/core/src/lambda/config/templates.ts
@@ -11,13 +11,13 @@ import * as _path from 'path'
 import * as vscode from 'vscode'
 import * as nls from 'vscode-nls'
 import * as fsUtils from '../../shared/filesystemUtilities'
-import { getLogger, Logger } from '../../shared/logger'
+import { getLogger, Logger } from '../../shared/logger/logger'
 import { ReadonlyJsonObject } from '../../shared/sam/debugger/awsSamDebugConfiguration'
 import { getTabSizeSetting } from '../../shared/utilities/editorUtilities'
 import { getNormalizedRelativePath } from '../../shared/utilities/pathUtils'
 import { saveDocumentIfDirty } from '../../shared/utilities/textDocumentUtilities'
 import { access } from 'fs/promises'
-import { fs } from '../../shared'
+import { fs } from '../../shared/fs/fs'
 
 const localize = nls.loadMessageBundle()
 
diff --git a/packages/core/src/lambda/local/debugConfiguration.ts b/packages/core/src/lambda/local/debugConfiguration.ts
index b21599b0563..bfccf03b070 100644
--- a/packages/core/src/lambda/local/debugConfiguration.ts
+++ b/packages/core/src/lambda/local/debugConfiguration.ts
@@ -18,7 +18,7 @@ import { tryGetAbsolutePath } from '../../shared/utilities/workspaceUtils'
 import { Architecture, RuntimeFamily } from '../models/samLambdaRuntime'
 import { SamLaunchRequestArgs } from '../../shared/sam/debugger/awsSamDebugger'
 
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import globals from '../../shared/extensionGlobals'
 
 /**
diff --git a/packages/core/src/lambda/utils.ts b/packages/core/src/lambda/utils.ts
index 7fa56bc33e9..5018a221929 100644
--- a/packages/core/src/lambda/utils.ts
+++ b/packages/core/src/lambda/utils.ts
@@ -12,7 +12,7 @@ import * as vscode from 'vscode'
 import { CloudFormationClient } from '../shared/clients/cloudFormationClient'
 import { LambdaClient } from '../shared/clients/lambdaClient'
 import { getFamily, getNodeMajorVersion, RuntimeFamily } from './models/samLambdaRuntime'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { HttpResourceFetcher } from '../shared/resourcefetcher/httpResourceFetcher'
 import { FileResourceFetcher } from '../shared/resourcefetcher/fileResourceFetcher'
 import { sampleRequestManifestPath } from './constants'
diff --git a/packages/core/src/lambda/vue/configEditor/samInvokeBackend.ts b/packages/core/src/lambda/vue/configEditor/samInvokeBackend.ts
index 2c3c8ee40dd..b292c8ab93e 100644
--- a/packages/core/src/lambda/vue/configEditor/samInvokeBackend.ts
+++ b/packages/core/src/lambda/vue/configEditor/samInvokeBackend.ts
@@ -7,7 +7,7 @@ import * as path from 'path'
 import * as vscode from 'vscode'
 import * as nls from 'vscode-nls'
 import { LaunchConfiguration } from '../../../shared/debug/launchConfiguration'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { HttpResourceFetcher } from '../../../shared/resourcefetcher/httpResourceFetcher'
 import {
     AwsSamDebuggerConfiguration,
@@ -31,8 +31,8 @@ import globals from '../../../shared/extensionGlobals'
 import { VueWebview } from '../../../webviews/main'
 import { Commands } from '../../../shared/vscode/commands2'
 import { telemetry } from '../../../shared/telemetry/telemetry'
-import { fs } from '../../../shared'
-import { ToolkitError } from '../../../shared'
+import { fs } from '../../../shared/fs/fs'
+import { ToolkitError } from '../../../shared/errors'
 import { ResourceNode } from '../../../awsService/appBuilder/explorer/nodes/resourceNode'
 
 const localize = nls.loadMessageBundle()
diff --git a/packages/core/src/lambda/vue/remoteInvoke/invokeLambda.ts b/packages/core/src/lambda/vue/remoteInvoke/invokeLambda.ts
index 38b3700719c..aafde327d7f 100644
--- a/packages/core/src/lambda/vue/remoteInvoke/invokeLambda.ts
+++ b/packages/core/src/lambda/vue/remoteInvoke/invokeLambda.ts
@@ -11,7 +11,7 @@ import { DefaultLambdaClient, LambdaClient } from '../../../shared/clients/lambd
 import * as picker from '../../../shared/ui/picker'
 import { ExtContext } from '../../../shared/extensions'
 
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { HttpResourceFetcher } from '../../../shared/resourcefetcher/httpResourceFetcher'
 import { sampleRequestPath } from '../../constants'
 import { LambdaFunctionNode } from '../../explorer/lambdaFunctionNode'
@@ -20,15 +20,15 @@ import { getSampleLambdaPayloads, SampleRequest } from '../../utils'
 import * as nls from 'vscode-nls'
 import { VueWebview } from '../../../webviews/main'
 import { telemetry, Result } from '../../../shared/telemetry/telemetry'
-import { decodeBase64 } from '../../../shared'
 import {
     runSamCliRemoteTestEvents,
     SamCliRemoteTestEventsParameters,
     TestEventsOperation,
 } from '../../../shared/sam/cli/samCliRemoteTestEvent'
 import { getSamCliContext } from '../../../shared/sam/cli/samCliContext'
-import { ToolkitError } from '../../../shared'
+import { ToolkitError } from '../../../shared/errors'
 import { basename } from 'path'
+import { decodeBase64 } from '../../../shared/utilities/textUtilities'
 
 const localize = nls.loadMessageBundle()
 
diff --git a/packages/core/src/lambda/wizards/samDeployWizard.ts b/packages/core/src/lambda/wizards/samDeployWizard.ts
index 98047b75db1..a11b377eb5b 100644
--- a/packages/core/src/lambda/wizards/samDeployWizard.ts
+++ b/packages/core/src/lambda/wizards/samDeployWizard.ts
@@ -11,7 +11,7 @@ const localize = nls.loadMessageBundle()
 import * as path from 'path'
 import * as vscode from 'vscode'
 import * as localizedText from '../../shared/localizedText'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { createHelpButton } from '../../shared/ui/buttons'
 import * as input from '../../shared/ui/input'
 import * as picker from '../../shared/ui/picker'
diff --git a/packages/core/src/login/webview/commonAuthViewProvider.ts b/packages/core/src/login/webview/commonAuthViewProvider.ts
index 8f641acdb8d..c96b79bea8c 100644
--- a/packages/core/src/login/webview/commonAuthViewProvider.ts
+++ b/packages/core/src/login/webview/commonAuthViewProvider.ts
@@ -44,7 +44,7 @@ import { CodeCatalystAuthenticationProvider } from '../../codecatalyst/auth'
 import { telemetry } from '../../shared/telemetry/telemetry'
 import { AuthSources } from './util'
 import { AuthFlowStates } from './vue/types'
-import { getTelemetryMetadataForConn } from '../../auth'
+import { getTelemetryMetadataForConn } from '../../auth/connection'
 import { AuthUtil } from '../../codewhisperer/util/authUtil'
 
 export class CommonAuthViewProvider implements WebviewViewProvider {
diff --git a/packages/core/src/login/webview/util.ts b/packages/core/src/login/webview/util.ts
index 078e39d1d14..c526e387d31 100644
--- a/packages/core/src/login/webview/util.ts
+++ b/packages/core/src/login/webview/util.ts
@@ -4,7 +4,7 @@
  */
 
 import { cwQuickPickSource, cwTreeNodeSource, amazonQChatSource } from '../../codewhisperer/commands/types'
-import { ExtStartUpSources } from '../../shared/telemetry'
+import { ExtStartUpSources } from '../../shared/telemetry/util'
 import { vscodeComponent } from '../../shared/vscode/commands2'
 
 /**
diff --git a/packages/core/src/login/webview/vue/amazonq/backend_amazonq.ts b/packages/core/src/login/webview/vue/amazonq/backend_amazonq.ts
index e9e139c752b..83c511ad9f6 100644
--- a/packages/core/src/login/webview/vue/amazonq/backend_amazonq.ts
+++ b/packages/core/src/login/webview/vue/amazonq/backend_amazonq.ts
@@ -16,7 +16,7 @@ import { awsIdSignIn } from '../../../../codewhisperer/util/showSsoPrompt'
 import { connectToEnterpriseSso } from '../../../../codewhisperer/util/getStartUrl'
 import { activateExtension, isExtensionInstalled } from '../../../../shared/utilities/vsCodeUtils'
 import { VSCODE_EXTENSION_ID } from '../../../../shared/extensions'
-import { getLogger } from '../../../../shared/logger'
+import { getLogger } from '../../../../shared/logger/logger'
 import { debounce } from 'lodash'
 import { AuthError, AuthFlowState, userCancelled } from '../types'
 import { ToolkitError } from '../../../../shared/errors'
diff --git a/packages/core/src/login/webview/vue/backend.ts b/packages/core/src/login/webview/vue/backend.ts
index ed467175334..2b80013acca 100644
--- a/packages/core/src/login/webview/vue/backend.ts
+++ b/packages/core/src/login/webview/vue/backend.ts
@@ -24,7 +24,7 @@ import {
 } from '../../../auth/connection'
 import { Auth } from '../../../auth/auth'
 import { StaticProfile, StaticProfileKeyErrorMessage } from '../../../auth/credentials/types'
-import { telemetry } from '../../../shared/telemetry'
+import { telemetry } from '../../../shared/telemetry/telemetry'
 import { AuthAddConnection } from '../../../shared/telemetry/telemetry'
 import { AuthSources } from '../util'
 import { AuthEnabledFeatures, AuthError, AuthFlowState, AuthUiClick, userCancelled } from './types'
diff --git a/packages/core/src/login/webview/vue/toolkit/backend_toolkit.ts b/packages/core/src/login/webview/vue/toolkit/backend_toolkit.ts
index b50fe563745..6c147f5d313 100644
--- a/packages/core/src/login/webview/vue/toolkit/backend_toolkit.ts
+++ b/packages/core/src/login/webview/vue/toolkit/backend_toolkit.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import { tryAddCredentials } from '../../../../auth/utils'
-import { getLogger } from '../../../../shared/logger'
+import { getLogger } from '../../../../shared/logger/logger'
 import { CommonAuthWebview } from '../backend'
 import {
     AwsConnection,
@@ -19,7 +19,7 @@ import {
 import { Auth } from '../../../../auth/auth'
 import { CodeCatalystAuthenticationProvider } from '../../../../codecatalyst/auth'
 import { AuthError, AuthFlowState } from '../types'
-import { setContext } from '../../../../shared'
+import { setContext } from '../../../../shared/vscode/setContext'
 import { builderIdStartUrl } from '../../../../auth/sso/constants'
 
 export class ToolkitLoginWebview extends CommonAuthWebview {
diff --git a/packages/core/src/notifications/panelNode.ts b/packages/core/src/notifications/panelNode.ts
index 1e03ee72124..70a69873ee3 100644
--- a/packages/core/src/notifications/panelNode.ts
+++ b/packages/core/src/notifications/panelNode.ts
@@ -17,7 +17,7 @@ import { registerToolView } from '../awsexplorer/activationShared'
 import { readonlyDocument } from '../shared/utilities/textDocumentUtilities'
 import { openUrl } from '../shared/utilities/vsCodeUtils'
 import { telemetry } from '../shared/telemetry/telemetry'
-import { globals } from '../shared'
+import globals from '../shared/extensionGlobals'
 
 const localize = nls.loadMessageBundle()
 const logger = getLogger('notifications')
diff --git a/packages/core/src/shared/awsContext.ts b/packages/core/src/shared/awsContext.ts
index 62e271589a9..3d38978cbe6 100644
--- a/packages/core/src/shared/awsContext.ts
+++ b/packages/core/src/shared/awsContext.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 import * as AWS from '@aws-sdk/types'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { ClassToInterfaceType } from './utilities/tsUtils'
 import { CredentialsShim } from '../auth/deprecated/loginManager'
 export interface AwsContextCredentials {
diff --git a/packages/core/src/shared/clients/docdbClient.ts b/packages/core/src/shared/clients/docdbClient.ts
index 65665e3ea2d..a613071d26e 100644
--- a/packages/core/src/shared/clients/docdbClient.ts
+++ b/packages/core/src/shared/clients/docdbClient.ts
@@ -4,7 +4,7 @@
  */
 
 import globals from '../extensionGlobals'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { getUserAgent } from '../telemetry/util'
 import { ToolkitError } from '../errors'
 import { InterfaceNoSymbol } from '../utilities/tsUtils'
diff --git a/packages/core/src/shared/clients/ec2MetadataClient.ts b/packages/core/src/shared/clients/ec2MetadataClient.ts
index fd07de50c74..899adb6761c 100644
--- a/packages/core/src/shared/clients/ec2MetadataClient.ts
+++ b/packages/core/src/shared/clients/ec2MetadataClient.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { ClassToInterfaceType } from '../utilities/tsUtils'
 import { AWSError, MetadataService } from 'aws-sdk'
 
diff --git a/packages/core/src/shared/clients/iotClient.ts b/packages/core/src/shared/clients/iotClient.ts
index a926c5edfd3..45b9cbd4e4f 100644
--- a/packages/core/src/shared/clients/iotClient.ts
+++ b/packages/core/src/shared/clients/iotClient.ts
@@ -6,7 +6,7 @@
 import * as _ from 'lodash'
 import { Iot } from 'aws-sdk'
 import { parse } from '@aws-sdk/util-arn-parser'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { InterfaceNoSymbol } from '../utilities/tsUtils'
 import globals from '../extensionGlobals'
 
diff --git a/packages/core/src/shared/clients/lambdaClient.ts b/packages/core/src/shared/clients/lambdaClient.ts
index 808a7ec6854..331564521ee 100644
--- a/packages/core/src/shared/clients/lambdaClient.ts
+++ b/packages/core/src/shared/clients/lambdaClient.ts
@@ -7,7 +7,7 @@ import { Lambda } from 'aws-sdk'
 import { _Blob } from 'aws-sdk/clients/lambda'
 import { ToolkitError } from '../errors'
 import globals from '../extensionGlobals'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { ClassToInterfaceType } from '../utilities/tsUtils'
 
 export type LambdaClient = ClassToInterfaceType<DefaultLambdaClient>
diff --git a/packages/core/src/shared/clients/s3Client.ts b/packages/core/src/shared/clients/s3Client.ts
index 950360caec5..d62ad279324 100644
--- a/packages/core/src/shared/clients/s3Client.ts
+++ b/packages/core/src/shared/clients/s3Client.ts
@@ -8,7 +8,7 @@ import * as url from 'url'
 import _ from 'lodash'
 import { AWSError, S3 } from 'aws-sdk'
 import { inspect } from 'util'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { bufferToStream, DefaultFileStreams, FileStreams, pipe } from '../utilities/streamUtilities'
 import { assertHasProps, InterfaceNoSymbol, isNonNullable, RequiredProps } from '../utilities/tsUtils'
 import { Readable } from 'stream'
diff --git a/packages/core/src/shared/cloudformation/activation.ts b/packages/core/src/shared/cloudformation/activation.ts
index 03d5b34e9d7..86cbf05698b 100644
--- a/packages/core/src/shared/cloudformation/activation.ts
+++ b/packages/core/src/shared/cloudformation/activation.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { isToolkitActive, localize } from '../utilities/vsCodeUtils'
 
 import { AsyncCloudFormationTemplateRegistry, CloudFormationTemplateRegistry } from '../fs/templateRegistry'
diff --git a/packages/core/src/shared/cloudformation/cloudformation.ts b/packages/core/src/shared/cloudformation/cloudformation.ts
index a22ff6d75b2..5d08bb836dc 100644
--- a/packages/core/src/shared/cloudformation/cloudformation.ts
+++ b/packages/core/src/shared/cloudformation/cloudformation.ts
@@ -9,7 +9,7 @@ import { schema } from 'yaml-cfn'
 import * as yaml from 'js-yaml'
 import * as filesystemUtilities from '../filesystemUtilities'
 import fs from '../../shared/fs/fs'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { lambdaPackageTypeImage } from '../constants'
 import { isUntitledScheme, normalizeVSCodeUri } from '../utilities/vsCodeUtils'
 
diff --git a/packages/core/src/shared/codelens/codeLensUtils.ts b/packages/core/src/shared/codelens/codeLensUtils.ts
index 5eb0c08fafe..f39391dd6de 100644
--- a/packages/core/src/shared/codelens/codeLensUtils.ts
+++ b/packages/core/src/shared/codelens/codeLensUtils.ts
@@ -8,7 +8,7 @@ import { RuntimeFamily } from '../../lambda/models/samLambdaRuntime'
 import * as CloudFormation from '../cloudformation/cloudformation'
 import { getResourcesForHandler } from '../fs/templateRegistry'
 import { LambdaHandlerCandidate } from '../lambdaHandlerSearch'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { API_TARGET_TYPE, CODE_TARGET_TYPE, TEMPLATE_TARGET_TYPE } from '../sam/debugger/awsSamDebugConfiguration'
 import {
     addSamDebugConfiguration,
diff --git a/packages/core/src/shared/crashMonitoring.ts b/packages/core/src/shared/crashMonitoring.ts
index 662a7907875..8d496f6a10f 100644
--- a/packages/core/src/shared/crashMonitoring.ts
+++ b/packages/core/src/shared/crashMonitoring.ts
@@ -9,12 +9,11 @@ import { getErrorId, getTelemetryReason, getTelemetryReasonDesc, isFileNotFoundE
 import { isAutomation, isDebugInstance } from './vscode/env'
 import { DevSettings } from './settings'
 import vscode from 'vscode'
-import { telemetry } from './telemetry'
-import { Logger } from './logger'
+import { telemetry } from './telemetry/telemetry'
+import { Logger, getLogger } from './logger/logger'
 import { isNewOsSession } from './utilities/osUtils'
 import nodeFs from 'fs/promises'
 import fs from './fs/fs'
-import { getLogger } from './logger/logger'
 import { crashMonitoringDirName } from './constants'
 import { throwOnUnstableFileSystem } from './filesystemUtilities'
 import { truncateUuid } from './crypto'
diff --git a/packages/core/src/shared/debug/launchConfiguration.ts b/packages/core/src/shared/debug/launchConfiguration.ts
index b76b134d9cb..69ea55366bb 100644
--- a/packages/core/src/shared/debug/launchConfiguration.ts
+++ b/packages/core/src/shared/debug/launchConfiguration.ts
@@ -22,7 +22,7 @@ import {
 } from '../sam/debugger/awsSamDebugConfigurationValidator'
 import * as pathutils from '../utilities/pathUtils'
 import { tryGetAbsolutePath } from '../utilities/workspaceUtils'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { makeFailedWriteMessage, showViewLogsMessage } from '../utilities/messages'
 import { openUrl } from '../utilities/vsCodeUtils'
 import globals from '../extensionGlobals'
diff --git a/packages/core/src/shared/extensionUtilities.ts b/packages/core/src/shared/extensionUtilities.ts
index 01d064f88b8..1e134aaa18f 100644
--- a/packages/core/src/shared/extensionUtilities.ts
+++ b/packages/core/src/shared/extensionUtilities.ts
@@ -7,7 +7,7 @@ import * as _ from 'lodash'
 import * as os from 'os'
 import * as vscode from 'vscode'
 import * as nls from 'vscode-nls'
-import { getLogger } from './logger'
+import { getLogger } from './logger/logger'
 import { VSCODE_EXTENSION_ID, extensionAlphaVersion } from './extensions'
 import { Ec2MetadataClient } from './clients/ec2MetadataClient'
 import { DefaultEc2MetadataClient } from './clients/ec2MetadataClient'
diff --git a/packages/core/src/shared/extensions/ssh.ts b/packages/core/src/shared/extensions/ssh.ts
index 1e75f9921aa..ba349a902c2 100644
--- a/packages/core/src/shared/extensions/ssh.ts
+++ b/packages/core/src/shared/extensions/ssh.ts
@@ -7,7 +7,7 @@ import * as vscode from 'vscode'
 import * as path from 'path'
 import * as nls from 'vscode-nls'
 import fs from '../fs/fs'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { ChildProcess, ChildProcessResult } from '../utilities/processUtils'
 import { ArrayConstructor, NonNullObject } from '../utilities/typeConstructors'
 import { Settings } from '../settings'
diff --git a/packages/core/src/shared/featureConfig.ts b/packages/core/src/shared/featureConfig.ts
index 1ef07968198..2c330648483 100644
--- a/packages/core/src/shared/featureConfig.ts
+++ b/packages/core/src/shared/featureConfig.ts
@@ -13,13 +13,13 @@ import * as vscode from 'vscode'
 import * as nls from 'vscode-nls'
 import { codeWhispererClient as client } from '../codewhisperer/client/codewhisperer'
 import { AuthUtil } from '../codewhisperer/util/authUtil'
-import { getLogger } from './logger'
+import { getLogger } from './logger/logger'
 import { isBuilderIdConnection, isIdcSsoConnection } from '../auth/connection'
 import { CodeWhispererSettings } from '../codewhisperer/util/codewhispererSettings'
 import globals from './extensionGlobals'
 import { getClientId, getOperatingSystem } from './telemetry/util'
 import { extensionVersion } from './vscode/env'
-import { telemetry } from './telemetry'
+import { telemetry } from './telemetry/telemetry'
 import { Commands } from './vscode/commands2'
 
 const localize = nls.loadMessageBundle()
diff --git a/packages/core/src/shared/filesystemUtilities.ts b/packages/core/src/shared/filesystemUtilities.ts
index d462d85ac15..54ca5b4b0e1 100644
--- a/packages/core/src/shared/filesystemUtilities.ts
+++ b/packages/core/src/shared/filesystemUtilities.ts
@@ -7,7 +7,7 @@ import * as crypto from 'crypto'
 import * as os from 'os'
 import * as path from 'path'
 import * as vscode from 'vscode'
-import { getLogger } from './logger'
+import { getLogger } from './logger/logger'
 import * as pathutils from './utilities/pathUtils'
 import globals from '../shared/extensionGlobals'
 import fs from '../shared/fs/fs'
diff --git a/packages/core/src/shared/fs/templateRegistry.ts b/packages/core/src/shared/fs/templateRegistry.ts
index 339c46b779f..00afe876c4d 100644
--- a/packages/core/src/shared/fs/templateRegistry.ts
+++ b/packages/core/src/shared/fs/templateRegistry.ts
@@ -12,7 +12,7 @@ import { isInDirectory } from '../filesystemUtilities'
 import { dotNetRuntimes, goRuntimes, javaRuntimes } from '../../lambda/models/samLambdaRuntime'
 import { getLambdaDetails } from '../../lambda/utils'
 import { WatchedFiles, WatchedItem } from './watchedFiles'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import globals from '../extensionGlobals'
 import { Timeout } from '../utilities/timeoutUtils'
 import { localize } from '../utilities/vsCodeUtils'
diff --git a/packages/core/src/shared/handleUninstall.ts b/packages/core/src/shared/handleUninstall.ts
index e6f9bb55478..9db90232bdc 100644
--- a/packages/core/src/shared/handleUninstall.ts
+++ b/packages/core/src/shared/handleUninstall.ts
@@ -10,7 +10,7 @@ import { existsSync } from 'fs' // eslint-disable-line no-restricted-imports
 import * as semver from 'semver'
 import { join } from 'path'
 import { getLogger } from './logger/logger'
-import { telemetry } from './telemetry'
+import { telemetry } from './telemetry/telemetry'
 import { VSCODE_EXTENSION_ID } from './extensions'
 
 /**
diff --git a/packages/core/src/shared/logger/activation.ts b/packages/core/src/shared/logger/activation.ts
index 9d590b226fd..644e3ae0adf 100644
--- a/packages/core/src/shared/logger/activation.ts
+++ b/packages/core/src/shared/logger/activation.ts
@@ -4,8 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { Logger, LogLevel, getLogger } from '.'
-import { fromVscodeLogLevel, setLogger } from './logger'
+import { Logger, LogLevel, getLogger, fromVscodeLogLevel, setLogger } from './logger'
 import { ToolkitLogger } from './toolkitLogger'
 import { Settings } from '../settings'
 import { Logging } from './commands'
diff --git a/packages/core/src/shared/logger/commands.ts b/packages/core/src/shared/logger/commands.ts
index f0a712b0f3f..03f7728a9c3 100644
--- a/packages/core/src/shared/logger/commands.ts
+++ b/packages/core/src/shared/logger/commands.ts
@@ -4,10 +4,9 @@
  */
 
 import * as vscode from 'vscode'
-import { Logger } from '.'
 import { telemetry } from '../telemetry/telemetry'
 import { Commands } from '../vscode/commands2'
-import { getLogger } from './logger'
+import { getLogger, Logger } from './logger'
 import globals from '../extensionGlobals'
 
 function revealLines(editor: vscode.TextEditor, start: number, end: number): void {
diff --git a/packages/core/src/shared/logger/index.ts b/packages/core/src/shared/logger/index.ts
index 400afafe0f3..71034fc002e 100644
--- a/packages/core/src/shared/logger/index.ts
+++ b/packages/core/src/shared/logger/index.ts
@@ -3,14 +3,4 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-// This file is the common import file, intended for use by most extension code.
-// It surfaces Logger and related interfaces, types, and retrieval.
-import * as logger from './logger'
-
-export type Loggable = Error | string
-
-export type Logger = logger.Logger
-export type LogLevel = logger.LogLevel
-export const getLogger = logger.getLogger
-export const getDebugConsoleLogger = logger.getDebugConsoleLogger
-export const getNullLogger = logger.getNullLogger
+export { Logger, LogLevel, getLogger, getDebugConsoleLogger, getNullLogger } from './logger'
diff --git a/packages/core/src/shared/logger/logger.ts b/packages/core/src/shared/logger/logger.ts
index 19be5ac2887..12069087f8b 100644
--- a/packages/core/src/shared/logger/logger.ts
+++ b/packages/core/src/shared/logger/logger.ts
@@ -271,3 +271,5 @@ export function getNullLogger(type?: 'debugConsole' | 'main'): Logger {
 export function setLogger(logger: Logger | undefined, type?: 'debugConsole' | 'main') {
     toolkitLoggers[type ?? 'main'] = logger
 }
+
+export type Loggable = Error | string
diff --git a/packages/core/src/shared/performance/performance.ts b/packages/core/src/shared/performance/performance.ts
index 39abd37b96f..b7049809b7d 100644
--- a/packages/core/src/shared/performance/performance.ts
+++ b/packages/core/src/shared/performance/performance.ts
@@ -4,7 +4,7 @@
  */
 
 import assert from 'assert'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 
 interface PerformanceMetrics {
     /**
diff --git a/packages/core/src/shared/regions/endpoints.ts b/packages/core/src/shared/regions/endpoints.ts
index 0111bebef19..64a36143187 100644
--- a/packages/core/src/shared/regions/endpoints.ts
+++ b/packages/core/src/shared/regions/endpoints.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 
 // Parses the endpoints.json file into a usable structure
 
diff --git a/packages/core/src/shared/regions/regionProvider.ts b/packages/core/src/shared/regions/regionProvider.ts
index 00d13942196..4269ff19c12 100644
--- a/packages/core/src/shared/regions/regionProvider.ts
+++ b/packages/core/src/shared/regions/regionProvider.ts
@@ -9,7 +9,7 @@ import * as nls from 'vscode-nls'
 const localize = nls.loadMessageBundle()
 
 import * as vscode from 'vscode'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { Endpoints, loadEndpoints, Region } from './endpoints'
 import { AwsContext } from '../awsContext'
 import { getIdeProperties, isAmazonQ } from '../extensionUtilities'
diff --git a/packages/core/src/shared/resourcefetcher/fileResourceFetcher.ts b/packages/core/src/shared/resourcefetcher/fileResourceFetcher.ts
index e4cf9c53040..e228fbe3e59 100644
--- a/packages/core/src/shared/resourcefetcher/fileResourceFetcher.ts
+++ b/packages/core/src/shared/resourcefetcher/fileResourceFetcher.ts
@@ -4,7 +4,7 @@
  */
 
 import fs from '../fs/fs'
-import { getLogger, Logger } from '../logger'
+import { getLogger, Logger } from '../logger/logger'
 import { ResourceFetcher } from './resourcefetcher'
 
 export class FileResourceFetcher implements ResourceFetcher {
diff --git a/packages/core/src/shared/resourcefetcher/httpResourceFetcher.ts b/packages/core/src/shared/resourcefetcher/httpResourceFetcher.ts
index e85e1ded70b..1a2300cdcb9 100644
--- a/packages/core/src/shared/resourcefetcher/httpResourceFetcher.ts
+++ b/packages/core/src/shared/resourcefetcher/httpResourceFetcher.ts
@@ -4,7 +4,7 @@
  */
 
 import { VSCODE_EXTENSION_ID } from '../extensions'
-import { getLogger, Logger } from '../logger'
+import { getLogger, Logger } from '../logger/logger'
 import { ResourceFetcher } from './resourcefetcher'
 import { Timeout, CancelEvent, waitUntil } from '../utilities/timeoutUtils'
 import request, { RequestError } from '../request'
diff --git a/packages/core/src/shared/resourcefetcher/node/httpResourceFetcher.ts b/packages/core/src/shared/resourcefetcher/node/httpResourceFetcher.ts
index d801e8c5027..eea3f9038c4 100644
--- a/packages/core/src/shared/resourcefetcher/node/httpResourceFetcher.ts
+++ b/packages/core/src/shared/resourcefetcher/node/httpResourceFetcher.ts
@@ -11,7 +11,7 @@ import got, { RequestError } from 'got'
 import urlToOptions from 'got/dist/source/core/utils/url-to-options'
 import Request from 'got/dist/source/core'
 import { VSCODE_EXTENSION_ID } from '../../extensions'
-import { getLogger, Logger } from '../../logger'
+import { getLogger, Logger } from '../../logger/logger'
 import { Timeout, CancellationError, CancelEvent } from '../../utilities/timeoutUtils'
 import { isCloud9 } from '../../extensionUtilities'
 import { Headers } from 'got/dist/source/core'
diff --git a/packages/core/src/shared/sam/cli/samCliBuild.ts b/packages/core/src/shared/sam/cli/samCliBuild.ts
index c2e9862a24b..128249c09c1 100644
--- a/packages/core/src/shared/sam/cli/samCliBuild.ts
+++ b/packages/core/src/shared/sam/cli/samCliBuild.ts
@@ -4,7 +4,7 @@
  */
 
 import { fileExists } from '../../filesystemUtilities'
-import { getLogger, Logger } from '../../logger'
+import { getLogger, Logger } from '../../logger/logger'
 import { logAndThrowIfUnexpectedExitCode, SamCliProcessInvoker } from './samCliInvokerUtils'
 import { pushIf } from '../../utilities/collectionUtils'
 import { localize } from '../../utilities/vsCodeUtils'
diff --git a/packages/core/src/shared/sam/cli/samCliInfo.ts b/packages/core/src/shared/sam/cli/samCliInfo.ts
index 8caed4c1e75..ededaa33c44 100644
--- a/packages/core/src/shared/sam/cli/samCliInfo.ts
+++ b/packages/core/src/shared/sam/cli/samCliInfo.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { getLogger, Logger } from '../../logger'
+import { getLogger, Logger } from '../../logger/logger'
 import { mergeResolvedShellPath } from '../../env/resolveEnv'
 import { ChildProcess } from '../../utilities/processUtils'
 
diff --git a/packages/core/src/shared/sam/cli/samCliInvoker.ts b/packages/core/src/shared/sam/cli/samCliInvoker.ts
index 979607e3fe7..03d6fa249d4 100644
--- a/packages/core/src/shared/sam/cli/samCliInvoker.ts
+++ b/packages/core/src/shared/sam/cli/samCliInvoker.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import * as logger from '../../logger'
+import * as logger from '../../logger/logger'
 import { ChildProcess, ChildProcessResult } from '../../utilities/processUtils'
 import {
     addTelemetryEnvVar,
diff --git a/packages/core/src/shared/sam/cli/samCliInvokerUtils.ts b/packages/core/src/shared/sam/cli/samCliInvokerUtils.ts
index e307c15a102..a042d74215d 100644
--- a/packages/core/src/shared/sam/cli/samCliInvokerUtils.ts
+++ b/packages/core/src/shared/sam/cli/samCliInvokerUtils.ts
@@ -4,7 +4,7 @@
  */
 
 import { SpawnOptions } from 'child_process' // eslint-disable-line no-restricted-imports
-import { getLogger } from '../../logger'
+import { getLogger } from '../../logger/logger'
 import { getUserAgent } from '../../telemetry/util'
 import { ChildProcessResult, ChildProcessOptions } from '../../utilities/processUtils'
 import { ErrorInformation, ToolkitError } from '../../errors'
diff --git a/packages/core/src/shared/sam/cli/samCliListResources.ts b/packages/core/src/shared/sam/cli/samCliListResources.ts
index ff73f19776b..341a48c30d6 100644
--- a/packages/core/src/shared/sam/cli/samCliListResources.ts
+++ b/packages/core/src/shared/sam/cli/samCliListResources.ts
@@ -6,7 +6,7 @@
 import * as vscode from 'vscode'
 import { logAndThrowIfUnexpectedExitCode, SamCliProcessInvoker } from './samCliInvokerUtils'
 import { getSpawnEnv } from '../../env/resolveEnv'
-import { getLogger } from '../..'
+import { getLogger } from '../../logger/logger'
 
 export interface SamCliListResourcesParameters {
     templateFile: string
diff --git a/packages/core/src/shared/sam/cli/samCliLocalInvoke.ts b/packages/core/src/shared/sam/cli/samCliLocalInvoke.ts
index 7905e80321e..d1139b6d819 100644
--- a/packages/core/src/shared/sam/cli/samCliLocalInvoke.ts
+++ b/packages/core/src/shared/sam/cli/samCliLocalInvoke.ts
@@ -6,7 +6,7 @@
 import { SpawnOptions } from 'child_process' // eslint-disable-line no-restricted-imports
 import { pushIf } from '../../utilities/collectionUtils'
 import * as nls from 'vscode-nls'
-import { getLogger, getDebugConsoleLogger, Logger } from '../../logger'
+import { getLogger, getDebugConsoleLogger, Logger } from '../../logger/logger'
 import { ChildProcess } from '../../utilities/processUtils'
 import { Timeout } from '../../utilities/timeoutUtils'
 import { removeAnsi } from '../../utilities/textUtilities'
diff --git a/packages/core/src/shared/sam/cli/samCliLocator.ts b/packages/core/src/shared/sam/cli/samCliLocator.ts
index 87fe474c76e..d71110cc45e 100644
--- a/packages/core/src/shared/sam/cli/samCliLocator.ts
+++ b/packages/core/src/shared/sam/cli/samCliLocator.ts
@@ -6,7 +6,7 @@
 import * as path from 'path'
 import { EnvironmentVariables } from '../../environmentVariables'
 import * as filesystemUtilities from '../../filesystemUtilities'
-import { getLogger, Logger } from '../../logger'
+import { getLogger, Logger } from '../../logger/logger'
 import { SamCliInfoInvocation } from './samCliInfo'
 import { DefaultSamCliValidator, SamCliValidatorContext, SamCliVersionValidation } from './samCliValidator'
 import { PerfLog } from '../../logger/perfLogger'
diff --git a/packages/core/src/shared/sam/cli/samCliRemoteTestEvent.ts b/packages/core/src/shared/sam/cli/samCliRemoteTestEvent.ts
index b09136f0c87..7c3d79ca9f2 100644
--- a/packages/core/src/shared/sam/cli/samCliRemoteTestEvent.ts
+++ b/packages/core/src/shared/sam/cli/samCliRemoteTestEvent.ts
@@ -8,7 +8,7 @@ import { logAndThrowIfUnexpectedExitCode, SamCliProcessInvoker } from './samCliI
 import path from 'path'
 import * as os from 'os'
 import { getSpawnEnv } from '../../env/resolveEnv'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 
 export const TestEventsOperation = {
     List: 'list',
diff --git a/packages/core/src/shared/sam/cli/samCliSettings.ts b/packages/core/src/shared/sam/cli/samCliSettings.ts
index 9562493a75b..693c3edb234 100644
--- a/packages/core/src/shared/sam/cli/samCliSettings.ts
+++ b/packages/core/src/shared/sam/cli/samCliSettings.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { getLogger } from '../../logger'
+import { getLogger } from '../../logger/logger'
 import { fromExtensionManifest, Settings } from '../../settings'
 import { stripUndefined, toRecord } from '../../utilities/collectionUtils'
 import { ClassToInterfaceType, keys } from '../../utilities/tsUtils'
diff --git a/packages/core/src/shared/sam/cli/samCliStartApi.ts b/packages/core/src/shared/sam/cli/samCliStartApi.ts
index 5521aa50371..3e0339ae258 100644
--- a/packages/core/src/shared/sam/cli/samCliStartApi.ts
+++ b/packages/core/src/shared/sam/cli/samCliStartApi.ts
@@ -4,7 +4,7 @@
  */
 
 import { fileExists } from '../../filesystemUtilities'
-import { getLogger } from '../../logger'
+import { getLogger } from '../../logger/logger'
 import { pushIf } from '../../utilities/collectionUtils'
 
 export interface SamCliStartApiArguments {
diff --git a/packages/core/src/shared/sam/debugger/awsSamDebugConfiguration.ts b/packages/core/src/shared/sam/debugger/awsSamDebugConfiguration.ts
index 4bf40211fa5..389b91f6208 100644
--- a/packages/core/src/shared/sam/debugger/awsSamDebugConfiguration.ts
+++ b/packages/core/src/shared/sam/debugger/awsSamDebugConfiguration.ts
@@ -13,7 +13,7 @@ import {
     CodeTargetProperties,
     TemplateTargetProperties,
 } from './awsSamDebugConfiguration.gen'
-import { getLogger } from '../../logger'
+import { getLogger } from '../../logger/logger'
 
 export * from './awsSamDebugConfiguration.gen'
 
diff --git a/packages/core/src/shared/sam/debugger/awsSamDebugger.ts b/packages/core/src/shared/sam/debugger/awsSamDebugger.ts
index f0c277285ac..2b6e9311e6b 100644
--- a/packages/core/src/shared/sam/debugger/awsSamDebugger.ts
+++ b/packages/core/src/shared/sam/debugger/awsSamDebugger.ts
@@ -33,7 +33,7 @@ import * as tsDebug from './typescriptSamDebug'
 import * as goDebug from './goSamDebug'
 import { ExtContext } from '../../extensions'
 import { isInDirectory, makeTemporaryToolkitFolder } from '../../filesystemUtilities'
-import { getLogger } from '../../logger'
+import { getLogger } from '../../logger/logger'
 import { getStartPort } from '../../utilities/debuggerUtils'
 import * as pathutil from '../../utilities/pathUtils'
 import { tryGetAbsolutePath } from '../../utilities/workspaceUtils'
diff --git a/packages/core/src/shared/sam/debugger/csharpSamDebug.ts b/packages/core/src/shared/sam/debugger/csharpSamDebug.ts
index e5c35e9146b..01aef679cd2 100644
--- a/packages/core/src/shared/sam/debugger/csharpSamDebug.ts
+++ b/packages/core/src/shared/sam/debugger/csharpSamDebug.ts
@@ -19,7 +19,7 @@ import { runLambdaFunction, waitForPort } from '../localLambdaRunner'
 import { SamLaunchRequestArgs } from './awsSamDebugger'
 import { ChildProcess } from '../../utilities/processUtils'
 import { HttpResourceFetcher } from '../../resourcefetcher/httpResourceFetcher'
-import { getLogger } from '../../logger'
+import { getLogger } from '../../logger/logger'
 import * as vscode from 'vscode'
 import * as nls from 'vscode-nls'
 import globals from '../../extensionGlobals'
diff --git a/packages/core/src/shared/sam/debugger/goSamDebug.ts b/packages/core/src/shared/sam/debugger/goSamDebug.ts
index 567ecaa18cb..d0d3ee2ed57 100644
--- a/packages/core/src/shared/sam/debugger/goSamDebug.ts
+++ b/packages/core/src/shared/sam/debugger/goSamDebug.ts
@@ -14,7 +14,7 @@ import { findParentProjectFile } from '../../utilities/workspaceUtils'
 import { DefaultSamLocalInvokeCommand, waitForDebuggerMessages } from '../cli/samCliLocalInvoke'
 import { runLambdaFunction } from '../localLambdaRunner'
 import { SamLaunchRequestArgs } from './awsSamDebugger'
-import { getLogger } from '../../logger'
+import { getLogger } from '../../logger/logger'
 import fs from '../../fs/fs'
 import { ChildProcess } from '../../utilities/processUtils'
 import { Timeout } from '../../utilities/timeoutUtils'
diff --git a/packages/core/src/shared/sam/debugger/pythonSamDebug.ts b/packages/core/src/shared/sam/debugger/pythonSamDebug.ts
index b802876c1cf..670c2ddd71a 100644
--- a/packages/core/src/shared/sam/debugger/pythonSamDebug.ts
+++ b/packages/core/src/shared/sam/debugger/pythonSamDebug.ts
@@ -15,7 +15,7 @@ import { RuntimeFamily } from '../../../lambda/models/samLambdaRuntime'
 import globals from '../../extensionGlobals'
 import { ExtContext } from '../../extensions'
 import { fileExists, readFileAsString } from '../../filesystemUtilities'
-import { getLogger } from '../../logger'
+import { getLogger } from '../../logger/logger'
 import * as pathutil from '../../utilities/pathUtils'
 import { getLocalRootVariants } from '../../utilities/pathUtils'
 import { DefaultSamLocalInvokeCommand, waitForDebuggerMessages } from '../cli/samCliLocalInvoke'
diff --git a/packages/core/src/shared/sam/debugger/typescriptSamDebug.ts b/packages/core/src/shared/sam/debugger/typescriptSamDebug.ts
index bd6785148db..e7ebece92e0 100644
--- a/packages/core/src/shared/sam/debugger/typescriptSamDebug.ts
+++ b/packages/core/src/shared/sam/debugger/typescriptSamDebug.ts
@@ -11,7 +11,7 @@ import { RuntimeFamily } from '../../../lambda/models/samLambdaRuntime'
 import { ChildProcess } from '../../utilities/processUtils'
 import * as pathutil from '../../../shared/utilities/pathUtils'
 import { ExtContext } from '../../extensions'
-import { getLogger } from '../../logger'
+import { getLogger } from '../../logger/logger'
 import { findParentProjectFile } from '../../utilities/workspaceUtils'
 import { DefaultSamLocalInvokeCommand, waitForDebuggerMessages } from '../cli/samCliLocalInvoke'
 import { runLambdaFunction, waitForPort } from '../localLambdaRunner'
diff --git a/packages/core/src/shared/sam/deploy.ts b/packages/core/src/shared/sam/deploy.ts
index a88e071f617..9d80ff9abd6 100644
--- a/packages/core/src/shared/sam/deploy.ts
+++ b/packages/core/src/shared/sam/deploy.ts
@@ -6,13 +6,14 @@
 import * as vscode from 'vscode'
 import { AWSTreeNodeBase } from '../treeview/nodes/awsTreeNodeBase'
 import { TreeNode, isTreeNode } from '../treeview/resourceTreeDataProvider'
-import { ToolkitError, globals } from '../../shared'
+import globals from '../../shared/extensionGlobals'
+import { ToolkitError } from '../../shared/errors'
 import { DefaultCloudFormationClient } from '../clients/cloudFormationClient'
 import { DefaultS3Client } from '../clients/s3Client'
 import { samDeployUrl } from '../constants'
 import { getSpawnEnv } from '../env/resolveEnv'
 import { CloudFormationTemplateRegistry } from '../fs/templateRegistry'
-import { telemetry } from '../telemetry'
+import { telemetry } from '../telemetry/telemetry'
 import { createExitPrompter } from '../ui/common/exitPrompter'
 import { createRegionPrompter } from '../ui/common/region'
 import { ChildProcess } from '../utilities/processUtils'
diff --git a/packages/core/src/shared/sam/localLambdaRunner.ts b/packages/core/src/shared/sam/localLambdaRunner.ts
index 25946299d6c..f560ca55f0c 100644
--- a/packages/core/src/shared/sam/localLambdaRunner.ts
+++ b/packages/core/src/shared/sam/localLambdaRunner.ts
@@ -12,7 +12,7 @@ import got, { OptionsOfTextResponseBody, RequestError } from 'got'
 import { isImageLambdaConfig } from '../../lambda/local/debugConfiguration'
 import { getFamily, RuntimeFamily } from '../../lambda/models/samLambdaRuntime'
 import { ExtContext } from '../extensions'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { SamTemplateGenerator } from '../templates/sam/samTemplateGenerator'
 import { Timeout } from '../utilities/timeoutUtils'
 import { tryGetAbsolutePath } from '../utilities/workspaceUtils'
diff --git a/packages/core/src/shared/sam/processTerminal.ts b/packages/core/src/shared/sam/processTerminal.ts
index a12dccb83d5..977fed9b02b 100644
--- a/packages/core/src/shared/sam/processTerminal.ts
+++ b/packages/core/src/shared/sam/processTerminal.ts
@@ -7,7 +7,7 @@ import * as vscode from 'vscode'
 import { ToolkitError, UnknownError } from '../errors'
 import { ChildProcess, ChildProcessResult } from '../utilities/processUtils'
 import { CancellationError } from '../utilities/timeoutUtils'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { isAutomation } from '../vscode/env'
 import { throwIfErrorMatches } from './utils'
 
diff --git a/packages/core/src/shared/sam/sync.ts b/packages/core/src/shared/sam/sync.ts
index 8c983ba67ad..a6b2d8aeca9 100644
--- a/packages/core/src/shared/sam/sync.ts
+++ b/packages/core/src/shared/sam/sync.ts
@@ -22,7 +22,7 @@ import { ToolkitError } from '../errors'
 import { telemetry } from '../telemetry/telemetry'
 import { createCommonButtons } from '../ui/buttons'
 import { ToolkitPromptSettings } from '../settings'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { createExitPrompter } from '../ui/common/exitPrompter'
 import { getConfigFileUri, SamConfig, validateSamSyncConfig, writeSamconfigGlobal } from './config'
 import { cast, Optional } from '../utilities/typeConstructors'
diff --git a/packages/core/src/shared/schemas.ts b/packages/core/src/shared/schemas.ts
index c75916fde68..1506908a7c8 100644
--- a/packages/core/src/shared/schemas.ts
+++ b/packages/core/src/shared/schemas.ts
@@ -7,7 +7,7 @@ import * as vscode from 'vscode'
 import globals from './extensionGlobals'
 import { activateYamlExtension, YamlExtension } from './extensions/yaml'
 import * as pathutil from '../shared/utilities/pathUtils'
-import { getLogger } from './logger'
+import { getLogger } from './logger/logger'
 import { FileResourceFetcher } from './resourcefetcher/fileResourceFetcher'
 import { getPropertyFromJsonUrl, HttpResourceFetcher } from './resourcefetcher/httpResourceFetcher'
 import { Settings } from './settings'
diff --git a/packages/core/src/shared/settings.ts b/packages/core/src/shared/settings.ts
index 5e157ba4605..a486784fe14 100644
--- a/packages/core/src/shared/settings.ts
+++ b/packages/core/src/shared/settings.ts
@@ -6,7 +6,7 @@
 import * as vscode from 'vscode'
 import * as codecatalyst from './clients/codecatalystClient'
 import * as codewhisperer from '../codewhisperer/client/codewhisperer'
-import { getLogger } from './logger'
+import { getLogger } from './logger/logger'
 import {
     cast,
     FromDescriptor,
diff --git a/packages/core/src/shared/sshConfig.ts b/packages/core/src/shared/sshConfig.ts
index 447648f879e..2c60b423ab3 100644
--- a/packages/core/src/shared/sshConfig.ts
+++ b/packages/core/src/shared/sshConfig.ts
@@ -6,7 +6,7 @@
 import * as vscode from 'vscode'
 import * as path from 'path'
 import * as nls from 'vscode-nls'
-import { getLogger } from './logger'
+import { getLogger } from './logger/logger'
 import { ChildProcess, ChildProcessResult } from './utilities/processUtils'
 import { Result } from './utilities/result'
 import { ToolkitError } from './errors'
diff --git a/packages/core/src/shared/telemetry/activation.ts b/packages/core/src/shared/telemetry/activation.ts
index f266787681c..2b0b2864ba1 100644
--- a/packages/core/src/shared/telemetry/activation.ts
+++ b/packages/core/src/shared/telemetry/activation.ts
@@ -11,7 +11,7 @@ const localize = nls.loadMessageBundle()
 import * as vscode from 'vscode'
 import { AwsContext } from '../awsContext'
 import { DefaultTelemetryService } from './telemetryService'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { getComputeRegion, isAmazonQ, productName } from '../extensionUtilities'
 import { openSettingsId, Settings } from '../settings'
 import { getSessionId, TelemetryConfig } from './util'
diff --git a/packages/core/src/shared/telemetry/telemetryClient.ts b/packages/core/src/shared/telemetry/telemetryClient.ts
index ebe2c1f9d02..139b4b48814 100644
--- a/packages/core/src/shared/telemetry/telemetryClient.ts
+++ b/packages/core/src/shared/telemetry/telemetryClient.ts
@@ -9,9 +9,8 @@ import { Credentials, Service } from 'aws-sdk'
 import * as os from 'os'
 import * as vscode from 'vscode'
 import { extensionVersion, isAutomation } from '../vscode/env'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import * as ClientTelemetry from './clienttelemetry'
-import { AWSProduct, MetricDatum } from './clienttelemetry'
 import apiConfig = require('./service-2.json')
 import { ServiceConfigurationOptions } from 'aws-sdk/lib/service'
 import globals from '../extensionGlobals'
@@ -57,9 +56,9 @@ export class DefaultTelemetryClient implements TelemetryClient {
     private static readonly defaultIdentityPool = 'us-east-1:820fd6d1-95c0-4ca4-bffb-3f01d32da842'
     private static readonly defaultTelemetryEndpoint = 'https://client-telemetry.us-east-1.amazonaws.com'
 
-    static #productName: AWSProduct
+    static #productName: ClientTelemetry.AWSProduct
 
-    public static set productName(val: AWSProduct) {
+    public static set productName(val: ClientTelemetry.AWSProduct) {
         getLogger().info(`Telemetry product: ${val}`)
         this.#productName = val
     }
@@ -93,7 +92,7 @@ export class DefaultTelemetryClient implements TelemetryClient {
      * Returns failed events
      * @param batch batch of events
      */
-    public async postMetrics(batch: MetricDatum[]): Promise<MetricDatum[] | undefined> {
+    public async postMetrics(batch: ClientTelemetry.MetricDatum[]): Promise<ClientTelemetry.MetricDatum[] | undefined> {
         try {
             // If our batching logic rejected all of the telemetry, don't try to post
             if (batch.length === 0) {
diff --git a/packages/core/src/shared/telemetry/telemetryLogger.ts b/packages/core/src/shared/telemetry/telemetryLogger.ts
index c01905f6260..bab7b3cc371 100644
--- a/packages/core/src/shared/telemetry/telemetryLogger.ts
+++ b/packages/core/src/shared/telemetry/telemetryLogger.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { DevSettings } from '../settings'
 import { isReleaseVersion } from '../vscode/env'
 import { MetricDatum, MetadataEntry } from './clienttelemetry'
diff --git a/packages/core/src/shared/telemetry/telemetryService.ts b/packages/core/src/shared/telemetry/telemetryService.ts
index 61e9559db7c..c3395be1120 100644
--- a/packages/core/src/shared/telemetry/telemetryService.ts
+++ b/packages/core/src/shared/telemetry/telemetryService.ts
@@ -7,7 +7,7 @@ import * as path from 'path'
 import { ExtensionContext } from 'vscode'
 import { AwsContext } from '../awsContext'
 import { isReleaseVersion, isAutomation } from '../vscode/env'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { MetricDatum } from './clienttelemetry'
 import { DefaultTelemetryClient, regionKey } from './telemetryClient'
 import { DefaultTelemetryPublisher } from './telemetryPublisher'
diff --git a/packages/core/src/shared/telemetry/util.ts b/packages/core/src/shared/telemetry/util.ts
index ce9342add56..c73a62a631f 100644
--- a/packages/core/src/shared/telemetry/util.ts
+++ b/packages/core/src/shared/telemetry/util.ts
@@ -6,7 +6,7 @@
 import * as vscode from 'vscode'
 import { env, version } from 'vscode'
 import * as os from 'os'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { fromExtensionManifest, Settings } from '../settings'
 import { memoize, once } from '../utilities/functionUtils'
 import {
diff --git a/packages/core/src/shared/treeview/resource.ts b/packages/core/src/shared/treeview/resource.ts
index 1f0fe77c0d4..58f68cab26a 100644
--- a/packages/core/src/shared/treeview/resource.ts
+++ b/packages/core/src/shared/treeview/resource.ts
@@ -12,7 +12,7 @@ import { once } from '../utilities/functionUtils'
 import { Commands } from '../vscode/commands2'
 import { TreeNode } from './resourceTreeDataProvider'
 import { createErrorItem, createPlaceholderItem } from './utils'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 
 interface SimpleResourceProvider<T = unknown> {
     readonly paginated?: false
diff --git a/packages/core/src/shared/treeview/utils.ts b/packages/core/src/shared/treeview/utils.ts
index 362e7050f49..94946883c05 100644
--- a/packages/core/src/shared/treeview/utils.ts
+++ b/packages/core/src/shared/treeview/utils.ts
@@ -7,7 +7,7 @@ import * as nls from 'vscode-nls'
 const localize = nls.loadMessageBundle()
 
 import * as vscode from 'vscode'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { AWSTreeNodeBase } from './nodes/awsTreeNodeBase'
 import { UnknownError } from '../errors'
 import { Logging } from '../logger/commands'
diff --git a/packages/core/src/shared/ui/common/regionSubmenu.ts b/packages/core/src/shared/ui/common/regionSubmenu.ts
index c8c054c57ea..a922ddf7583 100644
--- a/packages/core/src/shared/ui/common/regionSubmenu.ts
+++ b/packages/core/src/shared/ui/common/regionSubmenu.ts
@@ -11,7 +11,7 @@ import { createRegionPrompter } from './region'
 import { QuickPickPrompter } from '../pickerPrompter'
 import { Region } from '../../regions/endpoints'
 import { createRefreshButton } from '../buttons'
-import { getLogger } from '../../logger'
+import { getLogger } from '../../logger/logger'
 
 const switchRegion = Symbol('switchRegion')
 
diff --git a/packages/core/src/shared/ui/picker.ts b/packages/core/src/shared/ui/picker.ts
index 6a801cdf6ab..32f90421ba1 100644
--- a/packages/core/src/shared/ui/picker.ts
+++ b/packages/core/src/shared/ui/picker.ts
@@ -7,7 +7,7 @@ import * as vscode from 'vscode'
 import * as nls from 'vscode-nls'
 const localize = nls.loadMessageBundle()
 
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { IteratorTransformer } from '../utilities/collectionUtils'
 import { createRefreshButton } from './buttons'
 
diff --git a/packages/core/src/shared/ui/sam/templatePrompter.ts b/packages/core/src/shared/ui/sam/templatePrompter.ts
index a69a4b087bd..f51d1feaafc 100644
--- a/packages/core/src/shared/ui/sam/templatePrompter.ts
+++ b/packages/core/src/shared/ui/sam/templatePrompter.ts
@@ -5,7 +5,7 @@
 
 import * as path from 'path'
 import * as vscode from 'vscode'
-import { getSamInitDocUrl } from '../..'
+import { getSamInitDocUrl } from '../../extensionUtilities'
 import * as CloudFormation from '../../cloudformation/cloudformation'
 import { CloudFormationTemplateRegistry } from '../../fs/templateRegistry'
 import { createCommonButtons } from '../buttons'
diff --git a/packages/core/src/shared/utilities/cliUtils.ts b/packages/core/src/shared/utilities/cliUtils.ts
index b52ae10b023..a37a7228687 100644
--- a/packages/core/src/shared/utilities/cliUtils.ts
+++ b/packages/core/src/shared/utilities/cliUtils.ts
@@ -10,7 +10,7 @@ import * as path from 'path'
 import * as vscode from 'vscode'
 import { getIdeProperties } from '../extensionUtilities'
 import { makeTemporaryToolkitFolder, tryRemoveFolder } from '../filesystemUtilities'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { HttpResourceFetcher } from '../resourcefetcher/node/httpResourceFetcher'
 import { ChildProcess } from './processUtils'
 
diff --git a/packages/core/src/shared/utilities/commentUtils.ts b/packages/core/src/shared/utilities/commentUtils.ts
index 42854ec313c..690d0570dff 100644
--- a/packages/core/src/shared/utilities/commentUtils.ts
+++ b/packages/core/src/shared/utilities/commentUtils.ts
@@ -4,7 +4,7 @@
  */
 
 import vscode from 'vscode'
-import { CodeWhispererConstants } from '../../codewhisperer'
+import { SecurityScanLanguageId } from '../../codewhisperer/models/constants'
 
 interface CommentConfig {
     lineComment?: string
@@ -13,7 +13,7 @@ interface CommentConfig {
 
 const defaultCommentConfig: CommentConfig = { lineComment: '//', blockComment: ['/*', '*/'] }
 
-const languageCommentConfig: Record<CodeWhispererConstants.SecurityScanLanguageId, CommentConfig | undefined> = {
+const languageCommentConfig: Record<SecurityScanLanguageId, CommentConfig | undefined> = {
     java: defaultCommentConfig,
     python: { lineComment: '#', blockComment: ["'''", "'''"] },
     javascript: defaultCommentConfig,
@@ -50,7 +50,7 @@ const languageCommentConfig: Record<CodeWhispererConstants.SecurityScanLanguageI
 }
 
 export function getLanguageCommentConfig(languageId: string): CommentConfig {
-    return languageCommentConfig[languageId as CodeWhispererConstants.SecurityScanLanguageId] ?? {}
+    return languageCommentConfig[languageId as SecurityScanLanguageId] ?? {}
 }
 
 export function detectCommentAboveLine(document: vscode.TextDocument, line: number, comment: string): boolean {
diff --git a/packages/core/src/shared/utilities/diffUtils.ts b/packages/core/src/shared/utilities/diffUtils.ts
index 81e0af69000..f6dcd9d3fe4 100644
--- a/packages/core/src/shared/utilities/diffUtils.ts
+++ b/packages/core/src/shared/utilities/diffUtils.ts
@@ -10,7 +10,7 @@ import fs from '../fs/fs'
 import { amazonQDiffScheme } from '../constants'
 import { ContentProvider } from '../../amazonq/commons/controllers/contentController'
 import { disposeOnEditorClose } from './editorUtilities'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 
 /**
  * Get the patched code from a file and a patch.
diff --git a/packages/core/src/shared/utilities/logAndShowUtils.ts b/packages/core/src/shared/utilities/logAndShowUtils.ts
index 35339dd843c..3cccea1045b 100644
--- a/packages/core/src/shared/utilities/logAndShowUtils.ts
+++ b/packages/core/src/shared/utilities/logAndShowUtils.ts
@@ -6,7 +6,7 @@
 import * as vscode from 'vscode'
 import * as nls from 'vscode-nls'
 import { ToolkitError, isUserCancelledError, resolveErrorMessageToDisplay } from '../errors'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { showMessageWithUrl } from './messages'
 import { Logging } from '../logger/commands'
 
diff --git a/packages/core/src/shared/utilities/map.ts b/packages/core/src/shared/utilities/map.ts
index 1a681235cd4..57d20c1c590 100644
--- a/packages/core/src/shared/utilities/map.ts
+++ b/packages/core/src/shared/utilities/map.ts
@@ -4,7 +4,7 @@
  */
 
 import _ from 'lodash'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import type { KeyedCache } from './cacheUtils'
 
 /**
diff --git a/packages/core/src/shared/utilities/messages.ts b/packages/core/src/shared/utilities/messages.ts
index 54085407d65..fe2b08e42cf 100644
--- a/packages/core/src/shared/utilities/messages.ts
+++ b/packages/core/src/shared/utilities/messages.ts
@@ -6,7 +6,7 @@
 import * as vscode from 'vscode'
 import * as nls from 'vscode-nls'
 import * as localizedText from '../localizedText'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { ProgressEntry } from '../../shared/vscode/window'
 import { getIdeProperties } from '../extensionUtilities'
 import { sleep } from './timeoutUtils'
diff --git a/packages/core/src/shared/utilities/processUtils.ts b/packages/core/src/shared/utilities/processUtils.ts
index 488ebe14e7b..e7af78eaaea 100644
--- a/packages/core/src/shared/utilities/processUtils.ts
+++ b/packages/core/src/shared/utilities/processUtils.ts
@@ -5,10 +5,9 @@
 
 import * as proc from 'child_process' // eslint-disable-line no-restricted-imports
 import * as crossSpawn from 'cross-spawn'
-import * as logger from '../logger'
+import * as logger from '../logger/logger'
 import { Timeout, CancellationError, waitUntil } from './timeoutUtils'
 import { PollingSet } from './pollingSet'
-import { getLogger } from '../logger/logger'
 
 export interface RunParameterContext {
     /** Reports an error parsed from the stdin/stdout streams. */
@@ -73,7 +72,7 @@ export class ChildProcessTracker {
         memory: 100 * 1024 * 1024, // 100 MB
         cpu: 50,
     }
-    static readonly logger = getLogger('childProcess')
+    static readonly logger = logger.getLogger('childProcess')
     #processByPid: Map<number, ChildProcess> = new Map<number, ChildProcess>()
     #pids: PollingSet<number>
 
diff --git a/packages/core/src/shared/utilities/textDocumentUtilities.ts b/packages/core/src/shared/utilities/textDocumentUtilities.ts
index 1f2fb7aa1da..48a20a6c44b 100644
--- a/packages/core/src/shared/utilities/textDocumentUtilities.ts
+++ b/packages/core/src/shared/utilities/textDocumentUtilities.ts
@@ -7,7 +7,7 @@ import * as _path from 'path'
 import * as vscode from 'vscode'
 import { disposeOnEditorClose, getTabSizeSetting } from './editorUtilities'
 import { tempDirPath } from '../filesystemUtilities'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import fs from '../fs/fs'
 import { ToolkitError } from '../errors'
 import { indent } from './textUtilities'
diff --git a/packages/core/src/shared/utilities/textUtilities.ts b/packages/core/src/shared/utilities/textUtilities.ts
index b17b79517b8..e5746df0983 100644
--- a/packages/core/src/shared/utilities/textUtilities.ts
+++ b/packages/core/src/shared/utilities/textUtilities.ts
@@ -7,7 +7,7 @@ import * as vscode from 'vscode'
 import * as crypto from 'crypto'
 import * as fs from 'fs' // eslint-disable-line no-restricted-imports
 import { default as stripAnsi } from 'strip-ansi'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 
 /**
  * Truncates string `s` if it exceeds `n` chars.
diff --git a/packages/core/src/shared/utilities/workspaceUtils.ts b/packages/core/src/shared/utilities/workspaceUtils.ts
index c650b886016..f624a3ad2e1 100644
--- a/packages/core/src/shared/utilities/workspaceUtils.ts
+++ b/packages/core/src/shared/utilities/workspaceUtils.ts
@@ -7,7 +7,7 @@ import * as vscode from 'vscode'
 import * as path from 'path'
 import * as os from 'os'
 import * as pathutils from '../../shared/utilities/pathUtils'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { isInDirectory } from '../filesystemUtilities'
 import { normalizedDirnameWithTrailingSlash, normalize } from './pathUtils'
 import globals from '../extensionGlobals'
diff --git a/packages/core/src/shared/vscode/env.ts b/packages/core/src/shared/vscode/env.ts
index e9c8c1983b1..004db0efc27 100644
--- a/packages/core/src/shared/vscode/env.ts
+++ b/packages/core/src/shared/vscode/env.ts
@@ -7,7 +7,7 @@ import * as semver from 'semver'
 import * as vscode from 'vscode'
 import * as packageJson from '../../../package.json'
 import * as os from 'os'
-import { getLogger } from '../logger'
+import { getLogger } from '../logger/logger'
 import { onceChanged } from '../utilities/functionUtils'
 import { ChildProcess } from '../utilities/processUtils'
 import globals, { isWeb } from '../extensionGlobals'
diff --git a/packages/core/src/ssmDocument/commands/createDocumentFromTemplate.ts b/packages/core/src/ssmDocument/commands/createDocumentFromTemplate.ts
index 2d98ca24c48..418e5069c1e 100644
--- a/packages/core/src/ssmDocument/commands/createDocumentFromTemplate.ts
+++ b/packages/core/src/ssmDocument/commands/createDocumentFromTemplate.ts
@@ -9,7 +9,7 @@ const localize = nls.loadMessageBundle()
 import * as path from 'path'
 import * as vscode from 'vscode'
 import * as yaml from 'js-yaml'
-import { getLogger, Logger } from '../../shared/logger'
+import { getLogger, Logger } from '../../shared/logger/logger'
 import * as picker from '../../shared/ui/picker'
 import { promptUserForDocumentFormat } from '../util/util'
 import { readFileAsString } from '../../shared/filesystemUtilities'
diff --git a/packages/core/src/ssmDocument/commands/deleteDocument.ts b/packages/core/src/ssmDocument/commands/deleteDocument.ts
index 993413b6761..9ff836c4853 100644
--- a/packages/core/src/ssmDocument/commands/deleteDocument.ts
+++ b/packages/core/src/ssmDocument/commands/deleteDocument.ts
@@ -7,7 +7,7 @@ import * as nls from 'vscode-nls'
 const localize = nls.loadMessageBundle()
 
 import * as vscode from 'vscode'
-import { getLogger, Logger } from '../../shared/logger'
+import { getLogger, Logger } from '../../shared/logger/logger'
 import { DocumentItemNodeWriteable } from '../explorer/documentItemNodeWriteable'
 import { RegistryItemNode } from '../explorer/registryItemNode'
 import { showConfirmationMessage } from '../util/util'
diff --git a/packages/core/src/ssmDocument/commands/openDocumentItem.ts b/packages/core/src/ssmDocument/commands/openDocumentItem.ts
index 9b6793b76d0..af0c6760358 100644
--- a/packages/core/src/ssmDocument/commands/openDocumentItem.ts
+++ b/packages/core/src/ssmDocument/commands/openDocumentItem.ts
@@ -10,7 +10,7 @@ import { SSM } from 'aws-sdk'
 import * as vscode from 'vscode'
 import { DocumentItemNode } from '../explorer/documentItemNode'
 import { AwsContext } from '../../shared/awsContext'
-import { getLogger, Logger } from '../../shared/logger'
+import { getLogger, Logger } from '../../shared/logger/logger'
 import * as picker from '../../shared/ui/picker'
 import { showViewLogsMessage } from '../../shared/utilities/messages'
 import { telemetry } from '../../shared/telemetry/telemetry'
diff --git a/packages/core/src/ssmDocument/commands/publishDocument.ts b/packages/core/src/ssmDocument/commands/publishDocument.ts
index bd1e400cc0f..402c86412a6 100644
--- a/packages/core/src/ssmDocument/commands/publishDocument.ts
+++ b/packages/core/src/ssmDocument/commands/publishDocument.ts
@@ -11,7 +11,7 @@ import { DefaultSsmDocumentClient, SsmDocumentClient } from '../../shared/client
 import { ssmJson, ssmYaml } from '../../shared/constants'
 
 import * as localizedText from '../../shared/localizedText'
-import { getLogger, Logger } from '../../shared/logger'
+import { getLogger, Logger } from '../../shared/logger/logger'
 import {
     PublishSSMDocumentAction,
     PublishSSMDocumentWizard,
diff --git a/packages/core/src/ssmDocument/commands/updateDocumentVersion.ts b/packages/core/src/ssmDocument/commands/updateDocumentVersion.ts
index 92e788bcb89..cb3c1577360 100644
--- a/packages/core/src/ssmDocument/commands/updateDocumentVersion.ts
+++ b/packages/core/src/ssmDocument/commands/updateDocumentVersion.ts
@@ -9,7 +9,7 @@ const localize = nls.loadMessageBundle()
 import { SSM } from 'aws-sdk'
 import * as vscode from 'vscode'
 import { AwsContext } from '../../shared/awsContext'
-import { getLogger, Logger } from '../../shared/logger'
+import { getLogger, Logger } from '../../shared/logger/logger'
 import * as picker from '../../shared/ui/picker'
 import { DocumentItemNodeWriteable } from '../explorer/documentItemNodeWriteable'
 import { showViewLogsMessage } from '../../shared/utilities/messages'
diff --git a/packages/core/src/stepFunctions/commands/createStateMachineFromTemplate.ts b/packages/core/src/stepFunctions/commands/createStateMachineFromTemplate.ts
index 13b95aef5f2..a5e8187e47f 100644
--- a/packages/core/src/stepFunctions/commands/createStateMachineFromTemplate.ts
+++ b/packages/core/src/stepFunctions/commands/createStateMachineFromTemplate.ts
@@ -10,7 +10,7 @@ import { dump, load } from 'js-yaml'
 import * as path from 'path'
 import * as vscode from 'vscode'
 import { readFileAsString } from '../../shared/filesystemUtilities'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import { CreateStateMachineWizard, TemplateFormats } from '../wizards/createStateMachineWizard'
 
 import { YAML_ASL, JSON_ASL } from '../constants/aslFormats'
diff --git a/packages/core/src/stepFunctions/commands/downloadStateMachineDefinition.ts b/packages/core/src/stepFunctions/commands/downloadStateMachineDefinition.ts
index eacf78554ab..b3fdc2edb83 100644
--- a/packages/core/src/stepFunctions/commands/downloadStateMachineDefinition.ts
+++ b/packages/core/src/stepFunctions/commands/downloadStateMachineDefinition.ts
@@ -12,12 +12,12 @@ import * as path from 'path'
 import * as vscode from 'vscode'
 import { DefaultStepFunctionsClient, StepFunctionsClient } from '../../shared/clients/stepFunctionsClient'
 
-import { getLogger, Logger } from '../../shared/logger'
+import { getLogger, Logger } from '../../shared/logger/logger'
 import { Result } from '../../shared/telemetry/telemetry'
 import { StateMachineNode } from '../explorer/stepFunctionsNodes'
 import { previewStateMachineCommand } from '../activation'
 import { telemetry } from '../../shared/telemetry/telemetry'
-import { fs } from '../../shared'
+import { fs } from '../../shared/fs/fs'
 
 export async function downloadStateMachineDefinition(params: {
     outputChannel: vscode.OutputChannel
diff --git a/packages/core/src/stepFunctions/commands/publishStateMachine.ts b/packages/core/src/stepFunctions/commands/publishStateMachine.ts
index b54d872f122..9a4e20dab86 100644
--- a/packages/core/src/stepFunctions/commands/publishStateMachine.ts
+++ b/packages/core/src/stepFunctions/commands/publishStateMachine.ts
@@ -8,7 +8,7 @@ import * as vscode from 'vscode'
 import * as nls from 'vscode-nls'
 import { AwsContext } from '../../shared/awsContext'
 import { DefaultStepFunctionsClient, StepFunctionsClient } from '../../shared/clients/stepFunctionsClient'
-import { getLogger, Logger } from '../../shared/logger'
+import { getLogger, Logger } from '../../shared/logger/logger'
 import { showViewLogsMessage } from '../../shared/utilities/messages'
 import { VALID_SFN_PUBLISH_FORMATS, YAML_FORMATS } from '../constants/aslFormats'
 import { refreshStepFunctionsTree } from '../explorer/stepFunctionsNodes'
diff --git a/packages/core/src/stepFunctions/commands/visualizeStateMachine/abstractAslVisualizationManager.ts b/packages/core/src/stepFunctions/commands/visualizeStateMachine/abstractAslVisualizationManager.ts
index 090ee2809dd..1c6eb55c26c 100644
--- a/packages/core/src/stepFunctions/commands/visualizeStateMachine/abstractAslVisualizationManager.ts
+++ b/packages/core/src/stepFunctions/commands/visualizeStateMachine/abstractAslVisualizationManager.ts
@@ -7,7 +7,7 @@ import * as vscode from 'vscode'
 import * as nls from 'vscode-nls'
 import { StateMachineGraphCache } from '../../utils'
 
-import { Logger } from '../../../shared/logger'
+import { Logger } from '../../../shared/logger/logger'
 import { AslVisualization } from './aslVisualization'
 
 const localize = nls.loadMessageBundle()
diff --git a/packages/core/src/stepFunctions/commands/visualizeStateMachine/aslVisualization.ts b/packages/core/src/stepFunctions/commands/visualizeStateMachine/aslVisualization.ts
index 56467343d15..69f145c3eaf 100644
--- a/packages/core/src/stepFunctions/commands/visualizeStateMachine/aslVisualization.ts
+++ b/packages/core/src/stepFunctions/commands/visualizeStateMachine/aslVisualization.ts
@@ -8,7 +8,7 @@ const localize = nls.loadMessageBundle()
 import { debounce } from 'lodash'
 import * as path from 'path'
 import * as vscode from 'vscode'
-import { getLogger, Logger } from '../../../shared/logger'
+import { getLogger, Logger } from '../../../shared/logger/logger'
 import { isDocumentValid } from '../../utils'
 import * as yaml from 'js-yaml'
 
diff --git a/packages/core/src/stepFunctions/commands/visualizeStateMachine/aslVisualizationCDKManager.ts b/packages/core/src/stepFunctions/commands/visualizeStateMachine/aslVisualizationCDKManager.ts
index 1b614656b69..ce8a05c0dfd 100644
--- a/packages/core/src/stepFunctions/commands/visualizeStateMachine/aslVisualizationCDKManager.ts
+++ b/packages/core/src/stepFunctions/commands/visualizeStateMachine/aslVisualizationCDKManager.ts
@@ -7,7 +7,7 @@ import * as vscode from 'vscode'
 
 import { AslVisualizationCDK } from './aslVisualizationCDK'
 import { AbstractAslVisualizationManager } from './abstractAslVisualizationManager'
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 
 export class AslVisualizationCDKManager extends AbstractAslVisualizationManager<AslVisualizationCDK> {
     protected readonly name: string = 'AslVisualizationCDKManager'
diff --git a/packages/core/src/stepFunctions/commands/visualizeStateMachine/aslVisualizationManager.ts b/packages/core/src/stepFunctions/commands/visualizeStateMachine/aslVisualizationManager.ts
index 9b299f76b5b..48b0e45ca92 100644
--- a/packages/core/src/stepFunctions/commands/visualizeStateMachine/aslVisualizationManager.ts
+++ b/packages/core/src/stepFunctions/commands/visualizeStateMachine/aslVisualizationManager.ts
@@ -7,7 +7,7 @@ import * as vscode from 'vscode'
 
 import { AbstractAslVisualizationManager } from './abstractAslVisualizationManager'
 import { AslVisualization } from './aslVisualization'
-import { getLogger, Logger } from '../../../shared/logger'
+import { getLogger, Logger } from '../../../shared/logger/logger'
 
 export class AslVisualizationManager extends AbstractAslVisualizationManager {
     protected readonly name: string = 'AslVisualizationManager'
diff --git a/packages/core/src/stepFunctions/commands/visualizeStateMachine/getStateMachineDefinitionFromCfnTemplate.ts b/packages/core/src/stepFunctions/commands/visualizeStateMachine/getStateMachineDefinitionFromCfnTemplate.ts
index 29b2dd817a1..d21a8cee52d 100644
--- a/packages/core/src/stepFunctions/commands/visualizeStateMachine/getStateMachineDefinitionFromCfnTemplate.ts
+++ b/packages/core/src/stepFunctions/commands/visualizeStateMachine/getStateMachineDefinitionFromCfnTemplate.ts
@@ -4,7 +4,7 @@
  */
 
 import * as fs from 'fs' // eslint-disable-line no-restricted-imports
-import { getLogger, Logger } from '../../../shared/logger'
+import { getLogger, Logger } from '../../../shared/logger/logger'
 
 /**
  * @param {string} uniqueIdentifier - unique identifier of state machine
diff --git a/packages/core/src/stepFunctions/utils.ts b/packages/core/src/stepFunctions/utils.ts
index 32f48faaeb2..bb687e96c4a 100644
--- a/packages/core/src/stepFunctions/utils.ts
+++ b/packages/core/src/stepFunctions/utils.ts
@@ -9,7 +9,7 @@ import { IAM, StepFunctions } from 'aws-sdk'
 import * as vscode from 'vscode'
 import { StepFunctionsClient } from '../shared/clients/stepFunctionsClient'
 import { fileExists } from '../shared/filesystemUtilities'
-import { getLogger, Logger } from '../shared/logger'
+import { getLogger, Logger } from '../shared/logger/logger'
 import {
     DiagnosticSeverity,
     DocumentLanguageSettings,
@@ -19,7 +19,7 @@ import {
 import { HttpResourceFetcher } from '../shared/resourcefetcher/httpResourceFetcher'
 import globals from '../shared/extensionGlobals'
 import { fromExtensionManifest } from '../shared/settings'
-import { fs } from '../shared'
+import { fs } from '../shared/fs/fs'
 
 const documentSettings: DocumentLanguageSettings = { comments: 'error', trailingCommas: 'error' }
 const languageService = getLanguageService({})
diff --git a/packages/core/src/stepFunctions/vue/executeStateMachine/executeStateMachine.ts b/packages/core/src/stepFunctions/vue/executeStateMachine/executeStateMachine.ts
index b7c1f83657f..a90349db539 100644
--- a/packages/core/src/stepFunctions/vue/executeStateMachine/executeStateMachine.ts
+++ b/packages/core/src/stepFunctions/vue/executeStateMachine/executeStateMachine.ts
@@ -8,7 +8,7 @@ const localize = nls.loadMessageBundle()
 
 import { DefaultStepFunctionsClient } from '../../../shared/clients/stepFunctionsClient'
 
-import { getLogger } from '../../../shared/logger'
+import { getLogger } from '../../../shared/logger/logger'
 import { Result } from '../../../shared/telemetry/telemetry'
 import { StateMachineNode } from '../../explorer/stepFunctionsNodes'
 import { ExtContext } from '../../../shared/extensions'
diff --git a/packages/core/src/test/testLogger.ts b/packages/core/src/test/testLogger.ts
index db9d460652c..af06b3b3cce 100644
--- a/packages/core/src/test/testLogger.ts
+++ b/packages/core/src/test/testLogger.ts
@@ -3,7 +3,7 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { Loggable, LogLevel } from '../shared/logger'
+import { Loggable, LogLevel } from '../shared/logger/logger'
 import { BaseLogger, compareLogLevel } from '../shared/logger/logger'
 import { Uri } from 'vscode'
 import util from 'util'
diff --git a/packages/core/src/threatComposer/handlers/logMessageHandler.ts b/packages/core/src/threatComposer/handlers/logMessageHandler.ts
index 8f88a2f15a4..85ed05af104 100644
--- a/packages/core/src/threatComposer/handlers/logMessageHandler.ts
+++ b/packages/core/src/threatComposer/handlers/logMessageHandler.ts
@@ -4,7 +4,7 @@
  */
 
 import { Command, LogMessage, Message, MessageType, WebviewContext } from '../types'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 import * as vscode from 'vscode'
 import { sendThreatComposerErrored } from './webviewTelemetryHandler'
 
diff --git a/packages/core/src/threatComposer/handlers/onFileChangedHandler.ts b/packages/core/src/threatComposer/handlers/onFileChangedHandler.ts
index bded740e3c7..6f40b8ddbd6 100644
--- a/packages/core/src/threatComposer/handlers/onFileChangedHandler.ts
+++ b/packages/core/src/threatComposer/handlers/onFileChangedHandler.ts
@@ -6,7 +6,7 @@
 import { Command, FileChangedMessage, MessageType, WebviewContext } from '../types'
 import vscode from 'vscode'
 import fs from '../../shared/fs/fs'
-import { getLogger } from '../../shared/logger'
+import { getLogger } from '../../shared/logger/logger'
 
 /**
  * Function to call when the text document has been modified
diff --git a/packages/core/src/threatComposer/threatComposerEditor.ts b/packages/core/src/threatComposer/threatComposerEditor.ts
index 7bab20ca1a2..6bfb9ce9732 100644
--- a/packages/core/src/threatComposer/threatComposerEditor.ts
+++ b/packages/core/src/threatComposer/threatComposerEditor.ts
@@ -12,7 +12,7 @@ import { telemetry } from '../shared/telemetry/telemetry'
 import { onFileChanged } from './handlers/onFileChangedHandler'
 import { onThemeChanged } from './handlers/onThemeChangedHandler'
 import { sendThreatComposerOpenCancelled } from './handlers/webviewTelemetryHandler'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 
 const localize = nls.loadMessageBundle()
 
diff --git a/packages/core/src/threatComposer/threatComposerEditorProvider.ts b/packages/core/src/threatComposer/threatComposerEditorProvider.ts
index ffa53aa9c80..a742e17b40c 100644
--- a/packages/core/src/threatComposer/threatComposerEditorProvider.ts
+++ b/packages/core/src/threatComposer/threatComposerEditorProvider.ts
@@ -7,7 +7,7 @@ import * as vscode from 'vscode'
 import * as nls from 'vscode-nls'
 import fs from '../shared/fs/fs'
 import request from '../shared/request'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { ThreatComposerEditor } from './threatComposerEditor'
 import { ToolkitError } from '../shared/errors'
 import { telemetry } from '../shared/telemetry/telemetry'
diff --git a/packages/core/src/webviews/server.ts b/packages/core/src/webviews/server.ts
index 8914afce6be..a80b44a8253 100644
--- a/packages/core/src/webviews/server.ts
+++ b/packages/core/src/webviews/server.ts
@@ -4,7 +4,7 @@
  */
 
 import * as vscode from 'vscode'
-import { getLogger } from '../shared/logger'
+import { getLogger } from '../shared/logger/logger'
 import { Message } from './client'
 import { AsyncResource } from 'async_hooks'
 import { ToolkitError } from '../shared/errors'
diff --git a/plugins/eslint-plugin-aws-toolkits/index.ts b/plugins/eslint-plugin-aws-toolkits/index.ts
index 87ee111c095..88afc893348 100644
--- a/plugins/eslint-plugin-aws-toolkits/index.ts
+++ b/plugins/eslint-plugin-aws-toolkits/index.ts
@@ -11,6 +11,7 @@ import NoStringExecForChildProcess from './lib/rules/no-string-exec-for-child-pr
 import NoConsoleLog from './lib/rules/no-console-log'
 import noJsonStringifyInLog from './lib/rules/no-json-stringify-in-log'
 import noPrintfMismatch from './lib/rules/no-printf-mismatch'
+import noIndexImport from './lib/rules/no-index-import'
 
 const rules = {
     'no-await-on-vscode-msg': NoAwaitOnVscodeMsg,
@@ -21,6 +22,7 @@ const rules = {
     'no-console-log': NoConsoleLog,
     'no-json-stringify-in-log': noJsonStringifyInLog,
     'no-printf-mismatch': noPrintfMismatch,
+    'no-index-import': noIndexImport,
 }
 
 export { rules }
diff --git a/plugins/eslint-plugin-aws-toolkits/lib/rules/no-index-import.ts b/plugins/eslint-plugin-aws-toolkits/lib/rules/no-index-import.ts
new file mode 100644
index 00000000000..caebd59e803
--- /dev/null
+++ b/plugins/eslint-plugin-aws-toolkits/lib/rules/no-index-import.ts
@@ -0,0 +1,95 @@
+/*!
+ * Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+import { ESLintUtils, TSESTree } from '@typescript-eslint/utils'
+import { Rule } from 'eslint'
+import path from 'path'
+// eslint-disable-next-line no-restricted-imports
+import * as fs from 'fs'
+
+export const errMsg =
+    'do not import from folders or index.ts files since it can cause circular dependencies. import from the file directly.'
+
+/**
+ * Prevents TS imports from index.ts in packages/core/src (test files ignored).
+ * It is easy to create cryptic circular dependency issues in packages/core due to the current import/export structure.
+ *
+ * Example:
+ * - index.ts
+ *     export Auth from './auth'
+ *     export Connection from './connection'
+ * - auth.ts
+ *     export class Auth
+ * - connection.ts
+ *     import { Auth } from '.'                // circular dependency
+ *     export type Connection
+ *
+ * This is a problem because connection.ts depends on index.ts to export 'Auth', which depends on connection.ts
+ * to export `Connection`.
+ */
+export default ESLintUtils.RuleCreator.withoutDocs({
+    meta: {
+        docs: {
+            description: 'disallow importing from index.ts files in packages/core/src/',
+            recommended: 'recommended',
+        },
+        messages: {
+            default: errMsg,
+        },
+        type: 'problem',
+        fixable: 'code',
+        schema: [],
+    },
+    defaultOptions: [],
+    create(context) {
+        const filePath = context.physicalFilename
+        if (!filePath.match(/packages\/core\/src\/(?!test)/)) {
+            // only trigger for import statements inside packages/core/ src files,
+            // but don't include test files
+            return {}
+        }
+
+        return {
+            ImportDeclaration(node: TSESTree.ImportDeclaration) {
+                const relativeImportPath = node.source.value
+
+                // likely importing from some external module or is an irrelevant file
+                if (
+                    !relativeImportPath.startsWith('.') ||
+                    ['.json', '.js', '.vue'].includes(path.extname(relativeImportPath))
+                ) {
+                    return
+                }
+
+                const absoluteImportPath = path
+                    .resolve(path.dirname(filePath), relativeImportPath)
+                    .replace(/(\.d)?\.ts/, '') // remove any .d.ts or .ts file extensions on the import (unlikely)
+
+                if (path.basename(absoluteImportPath) !== 'index') {
+                    // Not an index.ts file but is some typescript file.
+                    if (['.ts', '.d.ts'].some((e) => fs.existsSync(absoluteImportPath + e))) {
+                        return
+                    }
+
+                    // If it does not exist as a folder, then the path is simply wrong. Another, more descriptive error will surface instead.
+                    if (!fs.existsSync(absoluteImportPath)) {
+                        return
+                    }
+                }
+
+                return context.report({
+                    node: node.source,
+                    messageId: 'default',
+                    // TODO: We can add a fixer to resolve the import for us.
+                    // fix: (fixer) => {
+                    //     // somehow parse the exports of the imported index.ts file to get the actual export path,
+                    //     // then replace the index import with it.
+                    //     return fixer.replaceText(node.source, newImport)
+                    // },
+                })
+            },
+        }
+    },
+}) as unknown as Rule.RuleModule
diff --git a/plugins/eslint-plugin-aws-toolkits/test/resources/noIndexImports/index.ts b/plugins/eslint-plugin-aws-toolkits/test/resources/noIndexImports/index.ts
new file mode 100644
index 00000000000..86e8ab59505
--- /dev/null
+++ b/plugins/eslint-plugin-aws-toolkits/test/resources/noIndexImports/index.ts
@@ -0,0 +1,6 @@
+/*!
+ * Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+export { doNothing } from './utils'
diff --git a/plugins/eslint-plugin-aws-toolkits/test/resources/noIndexImports/types.d.ts b/plugins/eslint-plugin-aws-toolkits/test/resources/noIndexImports/types.d.ts
new file mode 100644
index 00000000000..f448ecf26f8
--- /dev/null
+++ b/plugins/eslint-plugin-aws-toolkits/test/resources/noIndexImports/types.d.ts
@@ -0,0 +1,6 @@
+/*!
+ * Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+export interface doNothing {}
diff --git a/plugins/eslint-plugin-aws-toolkits/test/resources/noIndexImports/utils.ts b/plugins/eslint-plugin-aws-toolkits/test/resources/noIndexImports/utils.ts
new file mode 100644
index 00000000000..6975f4fffdd
--- /dev/null
+++ b/plugins/eslint-plugin-aws-toolkits/test/resources/noIndexImports/utils.ts
@@ -0,0 +1,6 @@
+/*!
+ * Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+export function doNothing() {}
diff --git a/plugins/eslint-plugin-aws-toolkits/test/rules/no-index-import.test.ts b/plugins/eslint-plugin-aws-toolkits/test/rules/no-index-import.test.ts
new file mode 100644
index 00000000000..0185c544b92
--- /dev/null
+++ b/plugins/eslint-plugin-aws-toolkits/test/rules/no-index-import.test.ts
@@ -0,0 +1,93 @@
+/*!
+ * Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+import path from 'path'
+import { rules } from '../../index'
+import { errMsg } from '../../lib/rules/no-index-import'
+import { getRuleTester } from '../testUtil'
+
+// Linted files need `packages/core/src` in their filepaths for them to pass, but we are referencing test resource files
+// from this project directory. So, "inject" the expected substring into this filepath.
+const verboseFilePath = `${__dirname.replace('dist/', '')}/../../../../packages/core/src/../../../plugins/eslint-plugin-aws-toolkits/test/rules/${path.basename(__filename.replace('.js', '.ts'))}`
+
+getRuleTester().run('no-index-import', rules['no-index-import'], {
+    valid: [
+        {
+            code: "import { doNothing } from '../resources/noIndexImports/utils'",
+            filename: verboseFilePath,
+        },
+        {
+            code: "import { doNothing } from '../resources/noIndexImports/utils.ts'",
+            filename: verboseFilePath,
+        },
+        {
+            code: "import config from '.eslintrc'",
+            filename: 'packages/amazonq/src/test.ts',
+        },
+        {
+            code: "import ts from '@typescript'",
+            filename: verboseFilePath,
+        },
+        {
+            code: "import { doNothing } from '../resources/noIndexImports'",
+            filename: verboseFilePath.replace('packages/core/src/', 'packages/core/src/test/../'),
+        },
+        {
+            code: "import { doNothing } from '../resources/noIndexImports'",
+            filename: verboseFilePath.replace('packages/core/src/', 'packages/core/src/testInteg/../'),
+        },
+        {
+            code: "import { doNothing } from '../resources/noIndexImports/utils'",
+            filename: verboseFilePath.replace('packages/core/src/', 'packages/core/src/index/../'),
+        },
+        {
+            code: "import { doNothing } from '../resources/noIndexImports/types.d.ts'",
+            filename: verboseFilePath,
+        },
+        {
+            code: "import { doNothing } from '../resources/noIndexImports/types'",
+            filename: verboseFilePath,
+        },
+        {
+            code: "import { doNothing } from '../resources/noIndexImports/doesNotExist.json'",
+            filename: verboseFilePath,
+        },
+        {
+            code: "import { doNothing } from '../resources/noIndexImports/utils.js'",
+            filename: verboseFilePath,
+        },
+        {
+            code: "import { doNothing } from '../resources/noIndexImports/utils.vue'",
+            filename: verboseFilePath,
+        },
+        {
+            code: "import { doNothing } from '../resources/nonexistantpath'",
+            filename: verboseFilePath,
+        },
+    ],
+
+    invalid: [
+        {
+            code: "import { doNothing } from '../resources/noIndexImports'",
+            errors: [errMsg],
+            filename: verboseFilePath,
+        },
+        {
+            code: "import { doNothing } from '../resources/noIndexImports/'",
+            errors: [errMsg],
+            filename: verboseFilePath,
+        },
+        {
+            code: "import { doNothing } from '../resources/noIndexImports/index'",
+            errors: [errMsg],
+            filename: verboseFilePath,
+        },
+        {
+            code: "import { doNothing } from '../resources/noIndexImports/index.ts'",
+            errors: [errMsg],
+            filename: verboseFilePath,
+        },
+    ],
+})