diff --git a/packages/amazonq/.changes/next-release/Deprecation-4577def6-0191-48db-bec3-480b226285b8.json b/packages/amazonq/.changes/next-release/Deprecation-4577def6-0191-48db-bec3-480b226285b8.json
new file mode 100644
index 00000000000..78d58a5fbe6
--- /dev/null
+++ b/packages/amazonq/.changes/next-release/Deprecation-4577def6-0191-48db-bec3-480b226285b8.json
@@ -0,0 +1,4 @@
+{
+	"type": "Deprecation",
+	"description": "The next release of this extension will require VS Code 1.83.0 or newer."
+}
diff --git a/packages/amazonq/.changes/next-release/Feature-b02fae9d-cb44-4625-af37-0b119c18ef63.json b/packages/amazonq/.changes/next-release/Feature-b02fae9d-cb44-4625-af37-0b119c18ef63.json
new file mode 100644
index 00000000000..021933ef072
--- /dev/null
+++ b/packages/amazonq/.changes/next-release/Feature-b02fae9d-cb44-4625-af37-0b119c18ef63.json
@@ -0,0 +1,4 @@
+{
+	"type": "Feature",
+	"description": "Show a one-time warning if new VS Code is required"
+}
diff --git a/packages/amazonq/package.json b/packages/amazonq/package.json
index 7662b0ed006..d3c38c991a3 100644
--- a/packages/amazonq/package.json
+++ b/packages/amazonq/package.json
@@ -112,6 +112,10 @@
                             "type": "boolean",
                             "default": false
                         },
+                        "minIdeVersion": {
+                            "type": "boolean",
+                            "default": false
+                        },
                         "ssoCacheError": {
                             "type": "boolean",
                             "default": false
@@ -1046,6 +1050,6 @@
     },
     "engines": {
         "npm": "^10.1.0",
-        "vscode": "^1.83.0"
+        "vscode": "^1.68.0"
     }
 }
diff --git a/packages/amazonq/src/extension.ts b/packages/amazonq/src/extension.ts
index 8e16a262254..bc5c8ae34c8 100644
--- a/packages/amazonq/src/extension.ts
+++ b/packages/amazonq/src/extension.ts
@@ -40,6 +40,7 @@ import {
     placeholder,
     setContext,
     setupUninstallHandler,
+    maybeShowMinVscodeWarning,
 } from 'aws-core-vscode/shared'
 import { ExtStartUpSources, telemetry } from 'aws-core-vscode/telemetry'
 import { VSCODE_EXTENSION_ID } from 'aws-core-vscode/utils'
@@ -98,6 +99,8 @@ export async function activateAmazonQCommon(context: vscode.ExtensionContext, is
         }
     }
 
+    void maybeShowMinVscodeWarning('1.83.0')
+
     globals.machineId = await getMachineId()
     globals.awsContext = new DefaultAwsContext()
     globals.sdkClientBuilder = new DefaultAWSClientBuilder(globals.awsContext)
diff --git a/packages/core/package.json b/packages/core/package.json
index c549bbd9e53..74d0eb2011d 100644
--- a/packages/core/package.json
+++ b/packages/core/package.json
@@ -5,7 +5,7 @@
     "license": "Apache-2.0",
     "engines": {
         "npm": "^10.1.0",
-        "vscode": "^1.83.0"
+        "vscode": "^1.68.0"
     },
     "exports": {
         ".": "./dist/src/extension.js",
diff --git a/packages/core/src/extension.ts b/packages/core/src/extension.ts
index 468aa6c61a9..778c90969b2 100644
--- a/packages/core/src/extension.ts
+++ b/packages/core/src/extension.ts
@@ -55,7 +55,7 @@ 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, setupUninstallHandler } from './shared'
+import { getLogger, maybeShowMinVscodeWarning, setupUninstallHandler } from './shared'
 import { showViewLogsMessage } from './shared/utilities/messages'
 
 disableAwsSdkWarning()
@@ -102,6 +102,8 @@ export async function activateCommon(
         getLogger().error('fs.init: invalid home directory given by env vars: %O', homeDirLogs)
     }
 
+    void maybeShowMinVscodeWarning('1.83.0')
+
     if (isCloud9()) {
         vscode.window.withProgress = wrapWithProgressForCloud9(globals.outputChannel)
         context.subscriptions.push(
diff --git a/packages/core/src/shared/extensionStartup.ts b/packages/core/src/shared/extensionStartup.ts
index 3770fa65825..d10c194d503 100644
--- a/packages/core/src/shared/extensionStartup.ts
+++ b/packages/core/src/shared/extensionStartup.ts
@@ -6,14 +6,43 @@
 import * as _ from 'lodash'
 import * as path from 'path'
 import * as vscode from 'vscode'
+import * as semver from 'semver'
 import * as nls from 'vscode-nls'
 
 import { BaseTemplates } from './templates/baseTemplates'
 import { fs } from '../shared/fs/fs'
-import { getIdeProperties, isCloud9, isCn } from './extensionUtilities'
+import { getIdeProperties, getIdeType, isAmazonQ, isCloud9, isCn, productName } from './extensionUtilities'
+import * as localizedText from './localizedText'
+import { AmazonQPromptSettings, ToolkitPromptSettings } from './settings'
 
 const localize = nls.loadMessageBundle()
 
+/**
+ * Shows a (suppressible) warning if the current vscode version is older than `minVscode`.
+ */
+export async function maybeShowMinVscodeWarning(minVscode: string) {
+    const settings = isAmazonQ() ? AmazonQPromptSettings.instance : ToolkitPromptSettings.instance
+    if (!(await settings.isPromptEnabled('minIdeVersion'))) {
+        return
+    }
+    const updateButton = `Update ${vscode.env.appName}`
+    if (getIdeType() === 'vscode' && semver.lt(vscode.version, minVscode)) {
+        void vscode.window
+            .showWarningMessage(
+                `${productName()} will soon require VS Code ${minVscode} or newer. The currently running version ${vscode.version} will no longer receive updates.`,
+                updateButton,
+                localizedText.dontShow
+            )
+            .then(async (resp) => {
+                if (resp === updateButton) {
+                    await vscode.commands.executeCommand('update.checkForUpdate')
+                } else if (resp === localizedText.dontShow) {
+                    void settings.disablePrompt('minIdeVersion')
+                }
+            })
+    }
+}
+
 /**
  * Helper function to show a webview containing the quick start page
  *
diff --git a/packages/core/src/shared/extensionUtilities.ts b/packages/core/src/shared/extensionUtilities.ts
index a0c7bbd9bb9..1b30c22bbc8 100644
--- a/packages/core/src/shared/extensionUtilities.ts
+++ b/packages/core/src/shared/extensionUtilities.ts
@@ -58,36 +58,29 @@ export function commandsPrefix(): string {
     return isAmazonQ() ? 'Amazon Q' : getIdeProperties().company
 }
 
-export enum IDE {
-    vscode,
-    cloud9,
-    sagemaker,
-    unknown,
-}
-
 let computeRegion: string | undefined = notInitialized
 
-export function getIdeType(): IDE {
+export function getIdeType(): 'vscode' | 'cloud9' | 'sagemaker' | 'unknown' {
     const settings = DevSettings.instance
     if (
         vscode.env.appName === cloud9Appname ||
         vscode.env.appName === cloud9CnAppname ||
         settings.get('forceCloud9', false)
     ) {
-        return IDE.cloud9
+        return 'cloud9'
     }
 
     if (vscode.env.appName === sageMakerAppname) {
-        return IDE.sagemaker
+        return 'sagemaker'
     }
 
     // Theia doesn't necessarily have all env properties
     // so we should be defensive and assume appName is nullable.
     if (vscode.env.appName?.startsWith(vscodeAppname)) {
-        return IDE.vscode
+        return 'vscode'
     }
 
-    return IDE.unknown
+    return 'unknown'
 }
 
 interface IdeProperties {
@@ -112,12 +105,12 @@ export function getIdeProperties(): IdeProperties {
     }
 
     switch (getIdeType()) {
-        case IDE.cloud9:
+        case 'cloud9':
             if (isCn()) {
                 return createCloud9Properties(localize('AWS.title.cn', 'Amazon'))
             }
             return createCloud9Properties(company)
-        case IDE.sagemaker:
+        case 'sagemaker':
             if (isCn()) {
                 // check for cn region
                 return createSageMakerProperties(localize('AWS.title.cn', 'Amazon'))
@@ -155,7 +148,7 @@ function createCloud9Properties(company: string): IdeProperties {
  * Decides if the current system is (the specified flavor of) Cloud9.
  */
 export function isCloud9(flavor: 'classic' | 'codecatalyst' | 'any' = 'any'): boolean {
-    const cloud9 = getIdeType() === IDE.cloud9
+    const cloud9 = getIdeType() === 'cloud9'
     if (!cloud9 || flavor === 'any') {
         return cloud9
     }
diff --git a/packages/core/src/shared/index.ts b/packages/core/src/shared/index.ts
index a31c647e226..e60d18f84ff 100644
--- a/packages/core/src/shared/index.ts
+++ b/packages/core/src/shared/index.ts
@@ -14,7 +14,8 @@ export { activate as activateTelemetry } from './telemetry/activation'
 export { DefaultAwsContext } from './awsContext'
 export { DefaultAWSClientBuilder, ServiceOptions } from './awsClientBuilder'
 export { Settings } from './settings'
-export { initializeComputeRegion } from './extensionUtilities'
+export * from './extensionUtilities'
+export * from './extensionStartup'
 export { RegionProvider } from './regions/regionProvider'
 export { Commands } from './vscode/commands2'
 export { getMachineId } from './vscode/env'
diff --git a/packages/core/src/shared/sam/activation.ts b/packages/core/src/shared/sam/activation.ts
index 4ae45aee103..22e3016bedf 100644
--- a/packages/core/src/shared/sam/activation.ts
+++ b/packages/core/src/shared/sam/activation.ts
@@ -25,7 +25,7 @@ import * as goLensProvider from '../codelens/goCodeLensProvider'
 import { SamTemplateCodeLensProvider } from '../codelens/samTemplateCodeLensProvider'
 import * as jsLensProvider from '../codelens/typescriptCodeLensProvider'
 import { ExtContext, VSCODE_EXTENSION_ID } from '../extensions'
-import { getIdeProperties, getIdeType, IDE, isCloud9 } from '../extensionUtilities'
+import { getIdeProperties, getIdeType, isCloud9 } from '../extensionUtilities'
 import { getLogger } from '../logger/logger'
 import { PerfLog } from '../logger/perfLogger'
 import { NoopWatcher } from '../fs/watchedFiles'
@@ -324,7 +324,7 @@ async function createYamlExtensionPrompt(): Promise<void> {
     // not have a marketplace or contain the YAML plugin.
     if (
         (await settings.isPromptEnabled('yamlExtPrompt')) &&
-        getIdeType() === IDE.vscode &&
+        getIdeType() === 'vscode' &&
         !vscode.extensions.getExtension(VSCODE_EXTENSION_ID.yaml)
     ) {
         // Disposed immediately after showing one, so the user isn't prompted
diff --git a/packages/core/src/shared/settings-amazonq.gen.ts b/packages/core/src/shared/settings-amazonq.gen.ts
index 1579e16227c..4fbe8ab0005 100644
--- a/packages/core/src/shared/settings-amazonq.gen.ts
+++ b/packages/core/src/shared/settings-amazonq.gen.ts
@@ -17,6 +17,7 @@ export const amazonqSettings = {
         "codeWhispererConnectionExpired": {},
         "amazonQWelcomePage": {},
         "amazonQSessionConfigurationMessage": {},
+        "minIdeVersion": {},
         "ssoCacheError": {}
     },
     "amazonQ.showInlineCodeSuggestionsWithCodeReferences": {},
diff --git a/packages/core/src/shared/settings-toolkit.gen.ts b/packages/core/src/shared/settings-toolkit.gen.ts
index 2d33c3300c5..ea291352701 100644
--- a/packages/core/src/shared/settings-toolkit.gen.ts
+++ b/packages/core/src/shared/settings-toolkit.gen.ts
@@ -37,6 +37,7 @@ export const toolkitSettings = {
         "samcliConfirmDevStack": {},
         "remoteConnected": {},
         "codeCatalystConnectionExpired": {},
+        "minIdeVersion": {},
         "ssoCacheError": {}
     },
     "aws.experiments": {
diff --git a/packages/core/src/test/shared/extensionUtilities.test.ts b/packages/core/src/test/shared/extensionUtilities.test.ts
index 5acc9b0f205..255455a54f1 100644
--- a/packages/core/src/test/shared/extensionUtilities.test.ts
+++ b/packages/core/src/test/shared/extensionUtilities.test.ts
@@ -18,10 +18,20 @@ import { InstanceIdentity } from '../../shared/clients/ec2MetadataClient'
 import { extensionVersion } from '../../shared/vscode/env'
 import { sleep } from '../../shared/utilities/timeoutUtils'
 import globals from '../../shared/extensionGlobals'
-import { createQuickStartWebview } from '../../shared/extensionStartup'
+import { createQuickStartWebview, maybeShowMinVscodeWarning } from '../../shared/extensionStartup'
 import { fs } from '../../shared'
+import { getTestWindow } from './vscode/window'
 
 describe('extensionUtilities', function () {
+    it('maybeShowMinVscodeWarning', async () => {
+        const testVscodeVersion = '99.0.0'
+        await maybeShowMinVscodeWarning(testVscodeVersion)
+        const expectedMsg =
+            /will soon require .* 99\.0\.0 or newer. The currently running version .* will no longer receive updates./
+        const msg = await getTestWindow().waitForMessage(expectedMsg)
+        msg.close()
+    })
+
     describe('createQuickStartWebview', async function () {
         let context: FakeExtensionContext
         let tempDir: string | undefined
diff --git a/packages/toolkit/.changes/next-release/Deprecation-2df766d2-cbec-4fdc-bb69-80f90d9d15ef.json b/packages/toolkit/.changes/next-release/Deprecation-2df766d2-cbec-4fdc-bb69-80f90d9d15ef.json
new file mode 100644
index 00000000000..78d58a5fbe6
--- /dev/null
+++ b/packages/toolkit/.changes/next-release/Deprecation-2df766d2-cbec-4fdc-bb69-80f90d9d15ef.json
@@ -0,0 +1,4 @@
+{
+	"type": "Deprecation",
+	"description": "The next release of this extension will require VS Code 1.83.0 or newer."
+}
diff --git a/packages/toolkit/.changes/next-release/Feature-7dfff66e-77a0-478d-8b74-6f3990b85a16.json b/packages/toolkit/.changes/next-release/Feature-7dfff66e-77a0-478d-8b74-6f3990b85a16.json
new file mode 100644
index 00000000000..021933ef072
--- /dev/null
+++ b/packages/toolkit/.changes/next-release/Feature-7dfff66e-77a0-478d-8b74-6f3990b85a16.json
@@ -0,0 +1,4 @@
+{
+	"type": "Feature",
+	"description": "Show a one-time warning if new VS Code is required"
+}
diff --git a/packages/toolkit/package.json b/packages/toolkit/package.json
index 3e957178a01..43acf33053c 100644
--- a/packages/toolkit/package.json
+++ b/packages/toolkit/package.json
@@ -53,7 +53,7 @@
     "browser": "./dist/src/extensionWeb",
     "engines": {
         "npm": "^10.1.0",
-        "vscode": "^1.83.0"
+        "vscode": "^1.68.0"
     },
     "scripts": {
         "vscode:prepublish": "npm run clean && npm run buildScripts && webpack --mode production",
@@ -225,6 +225,10 @@
                             "type": "boolean",
                             "default": false
                         },
+                        "minIdeVersion": {
+                            "type": "boolean",
+                            "default": false
+                        },
                         "ssoCacheError": {
                             "type": "boolean",
                             "default": false