diff --git a/package-lock.json b/package-lock.json
index 41e5804b5..e26a4f180 100644
--- a/package-lock.json
+++ b/package-lock.json
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-      "integrity": "sha512-7++dFhtcx3353uBaq8DDR4NuxBetBzC7ZQOhmTQInHEd6bSrXdiEyzCvG07Z44UYdLShWUyXt5M/yhz8ekcb1A==",
-      "dev": true
+      "integrity": "sha512-7++dFhtcx3353uBaq8DDR4NuxBetBzC7ZQOhmTQInHEd6bSrXdiEyzCvG07Z44UYdLShWUyXt5M/yhz8ekcb1A=="
     },
     "shell-quote": {
       "version": "1.8.1",
@@ -24334,8 +24215,7 @@
     "signal-exit": {
       "version": "4.1.0",
       "resolved": "https://registry.npmjs.org/signal-exit/-/signal-exit-4.1.0.tgz",
-      "integrity": "sha512-bzyZ1e88w9O1iNJbKnOlvYTrWPDl46O1bG0D3XInv+9tkPrxrN8jUUTiFlDkkmKWgn1M6CfIA13SuGqOa9Korw==",
-      "dev": true
+      "integrity": "sha512-bzyZ1e88w9O1iNJbKnOlvYTrWPDl46O1bG0D3XInv+9tkPrxrN8jUUTiFlDkkmKWgn1M6CfIA13SuGqOa9Korw=="
     },
     "simple-concat": {
       "version": "1.0.1",
@@ -24606,7 +24486,6 @@
       "version": "2.18.0",
       "resolved": "https://registry.npmjs.org/streamx/-/streamx-2.18.0.tgz",
       "integrity": "sha512-LLUC1TWdjVdn1weXGcSxyTR3T4+acB6tVGXT95y0nGbca4t4o/ng1wKAGTljm9VicuCVLvRlqFYXYy5GwgM7sQ==",
-      "dev": true,
       "requires": {
         "bare-events": "^2.2.0",
         "fast-fifo": "^1.3.2",
@@ -24626,7 +24505,6 @@
       "version": "5.1.2",
       "resolved": "https://registry.npmjs.org/string-width/-/string-width-5.1.2.tgz",
       "integrity": "sha512-HnLOCR3vjcY8beoNLtcjZ5/nxn2afmME6lhrDrebokqMap+XbeW8n9TXpPDOqdGK5qcI3oT0GKTW6wC7EMiVqA==",
-      "dev": true,
       "requires": {
         "eastasianwidth": "^0.2.0",
         "emoji-regex": "^9.2.2",
@@ -24636,14 +24514,12 @@
         "ansi-regex": {
           "version": "6.0.1",
           "resolved": "https://registry.npmjs.org/ansi-regex/-/ansi-regex-6.0.1.tgz",
-          "integrity": "sha512-n5M855fKb2SsfMIiFFoVrABHJC8QtHwVx+mHWP3QcEqBHYienj5dHSgjbxtC0WEZXYt4wcD6zrQElDPhFuZgfA==",
-          "dev": true
+          "integrity": "sha512-n5M855fKb2SsfMIiFFoVrABHJC8QtHwVx+mHWP3QcEqBHYienj5dHSgjbxtC0WEZXYt4wcD6zrQElDPhFuZgfA=="
         },
         "strip-ansi": {
           "version": "7.1.0",
           "resolved": "https://registry.npmjs.org/strip-ansi/-/strip-ansi-7.1.0.tgz",
           "integrity": "sha512-iq6eVVI64nQQTRYq2KtEg2d2uU7LElhTJwsH4YzIHZshxlgZms/wIc4VoDQTlG/IvVIrBKG06CrZnp0qv7hkcQ==",
-          "dev": true,
           "requires": {
             "ansi-regex": "^6.0.1"
           }
@@ -24654,7 +24530,6 @@
       "version": "npm:string-width@4.2.3",
       "resolved": "https://registry.npmjs.org/string-width/-/string-width-4.2.3.tgz",
       "integrity": "sha512-wKyQRQpjJ0sIp62ErSZdGsjMJWsap5oRNihHhu6G7JVO/9jIB6UyevL+tXuOqrng8j/cxKTWyWUwvSTriiZz/g==",
-      "dev": true,
       "requires": {
         "emoji-regex": "^8.0.0",
         "is-fullwidth-code-point": "^3.0.0",
@@ -24664,8 +24539,7 @@
         "emoji-regex": {
           "version": "8.0.0",
           "resolved": "https://registry.npmjs.org/emoji-regex/-/emoji-regex-8.0.0.tgz",
-          "integrity": "sha512-MSjYzcWNOA0ewAHpz0MxpYFvwg6yjy1NG3xteoqz644VCo/RPgnr1/GGt+ic3iJTzQ8Eu3TdM14SawnVUmGE6A==",
-          "dev": true
+          "integrity": "sha512-MSjYzcWNOA0ewAHpz0MxpYFvwg6yjy1NG3xteoqz644VCo/RPgnr1/GGt+ic3iJTzQ8Eu3TdM14SawnVUmGE6A=="
         }
       }
     },
@@ -24719,7 +24593,6 @@
       "version": "6.0.1",
       "resolved": "https://registry.npmjs.org/strip-ansi/-/strip-ansi-6.0.1.tgz",
       "integrity": "sha512-Y38VPSHcqkFrCpFnQ9vuSXmquuv5oXOKpGeT6aGrr3o3Gc9AlVa6JBfUSOCnbxGGZF+/0ooI7KrPuUSztUdU5A==",
-      "dev": true,
       "requires": {
         "ansi-regex": "^5.0.1"
       }
@@ -24728,7 +24601,6 @@
       "version": "npm:strip-ansi@6.0.1",
       "resolved": "https://registry.npmjs.org/strip-ansi/-/strip-ansi-6.0.1.tgz",
       "integrity": "sha512-Y38VPSHcqkFrCpFnQ9vuSXmquuv5oXOKpGeT6aGrr3o3Gc9AlVa6JBfUSOCnbxGGZF+/0ooI7KrPuUSztUdU5A==",
-      "dev": true,
       "requires": {
         "ansi-regex": "^5.0.1"
       }
@@ -24935,7 +24807,6 @@
       "version": "1.1.1",
       "resolved": "https://registry.npmjs.org/text-decoder/-/text-decoder-1.1.1.tgz",
       "integrity": "sha512-8zll7REEv4GDD3x4/0pW+ppIxSNs7H1J10IKFZsuOMscumCdM2a+toDGLPA3T+1+fLBql4zbt5z83GEQGGV5VA==",
-      "dev": true,
       "requires": {
         "b4a": "^1.6.4"
       }
@@ -25900,7 +25771,6 @@
       "version": "2.0.2",
       "resolved": "https://registry.npmjs.org/which/-/which-2.0.2.tgz",
       "integrity": "sha512-BLI3Tl1TW3Pvl70l3yq3Y64i+awpwXqsGBYWkkqMtnbXgrMD+yj7rhW0kuEDxzJaYXGjEW5ogapKNMEKNMjibA==",
-      "dev": true,
       "requires": {
         "isexe": "^2.0.0"
       }
@@ -25985,7 +25855,6 @@
       "version": "8.1.0",
       "resolved": "https://registry.npmjs.org/wrap-ansi/-/wrap-ansi-8.1.0.tgz",
       "integrity": "sha512-si7QWI6zUMq56bESFvagtmzMdGOtoxfR+Sez11Mobfc7tm+VkUckk9bW2UeffTGVUbOksxmSw0AA2gs8g71NCQ==",
-      "dev": true,
       "requires": {
         "ansi-styles": "^6.1.0",
         "string-width": "^5.0.1",
@@ -25995,20 +25864,17 @@
         "ansi-regex": {
           "version": "6.0.1",
           "resolved": "https://registry.npmjs.org/ansi-regex/-/ansi-regex-6.0.1.tgz",
-          "integrity": "sha512-n5M855fKb2SsfMIiFFoVrABHJC8QtHwVx+mHWP3QcEqBHYienj5dHSgjbxtC0WEZXYt4wcD6zrQElDPhFuZgfA==",
-          "dev": true
+          "integrity": "sha512-n5M855fKb2SsfMIiFFoVrABHJC8QtHwVx+mHWP3QcEqBHYienj5dHSgjbxtC0WEZXYt4wcD6zrQElDPhFuZgfA=="
         },
         "ansi-styles": {
           "version": "6.2.1",
           "resolved": "https://registry.npmjs.org/ansi-styles/-/ansi-styles-6.2.1.tgz",
-          "integrity": "sha512-bN798gFfQX+viw3R7yrGWRqnrN2oRkEkUjjl4JNn4E8GxxbjtG3FbrEIIY3l8/hrwUwIeCZvi4QuOTP4MErVug==",
-          "dev": true
+          "integrity": "sha512-bN798gFfQX+viw3R7yrGWRqnrN2oRkEkUjjl4JNn4E8GxxbjtG3FbrEIIY3l8/hrwUwIeCZvi4QuOTP4MErVug=="
         },
         "strip-ansi": {
           "version": "7.1.0",
           "resolved": "https://registry.npmjs.org/strip-ansi/-/strip-ansi-7.1.0.tgz",
           "integrity": "sha512-iq6eVVI64nQQTRYq2KtEg2d2uU7LElhTJwsH4YzIHZshxlgZms/wIc4VoDQTlG/IvVIrBKG06CrZnp0qv7hkcQ==",
-          "dev": true,
           "requires": {
             "ansi-regex": "^6.0.1"
           }
@@ -26019,7 +25885,6 @@
       "version": "npm:wrap-ansi@7.0.0",
       "resolved": "https://registry.npmjs.org/wrap-ansi/-/wrap-ansi-7.0.0.tgz",
       "integrity": "sha512-YVGIj2kamLSTxw6NsZjoBxfSwsn0ycdesmc4p+Q21c5zPuZ1pl+NfxVdxPtdHvmNVOQ6XSYG4AUtyt/Fi7D16Q==",
-      "dev": true,
       "requires": {
         "ansi-styles": "^4.0.0",
         "string-width": "^4.1.0",
@@ -26029,14 +25894,12 @@
         "emoji-regex": {
           "version": "8.0.0",
           "resolved": "https://registry.npmjs.org/emoji-regex/-/emoji-regex-8.0.0.tgz",
-          "integrity": "sha512-MSjYzcWNOA0ewAHpz0MxpYFvwg6yjy1NG3xteoqz644VCo/RPgnr1/GGt+ic3iJTzQ8Eu3TdM14SawnVUmGE6A==",
-          "dev": true
+          "integrity": "sha512-MSjYzcWNOA0ewAHpz0MxpYFvwg6yjy1NG3xteoqz644VCo/RPgnr1/GGt+ic3iJTzQ8Eu3TdM14SawnVUmGE6A=="
         },
         "string-width": {
           "version": "4.2.3",
           "resolved": "https://registry.npmjs.org/string-width/-/string-width-4.2.3.tgz",
           "integrity": "sha512-wKyQRQpjJ0sIp62ErSZdGsjMJWsap5oRNihHhu6G7JVO/9jIB6UyevL+tXuOqrng8j/cxKTWyWUwvSTriiZz/g==",
-          "dev": true,
           "requires": {
             "emoji-regex": "^8.0.0",
             "is-fullwidth-code-point": "^3.0.0",
@@ -26172,7 +26035,6 @@
       "version": "6.0.1",
       "resolved": "https://registry.npmjs.org/zip-stream/-/zip-stream-6.0.1.tgz",
       "integrity": "sha512-zK7YHHz4ZXpW89AHXUPbQVGKI7uvkd3hzusTdotCg1UxyaVtg0zFJSTfW/Dq5f7OBBVnq6cZIaC8Ti4hb6dtCA==",
-      "dev": true,
       "requires": {
         "archiver-utils": "^5.0.0",
         "compress-commons": "^6.0.2",
@@ -26183,7 +26045,6 @@
           "version": "6.0.3",
           "resolved": "https://registry.npmjs.org/buffer/-/buffer-6.0.3.tgz",
           "integrity": "sha512-FTiCpNxtwiZZHEZbcbTIcZjERVICn9yq/pDFkTl95/AxzD1naBctN7YO68riM/gLSDY7sdrMby8hofADYuuqOA==",
-          "dev": true,
           "requires": {
             "base64-js": "^1.3.1",
             "ieee754": "^1.2.1"
@@ -26193,7 +26054,6 @@
           "version": "4.5.2",
           "resolved": "https://registry.npmjs.org/readable-stream/-/readable-stream-4.5.2.tgz",
           "integrity": "sha512-yjavECdqeZ3GLXNgRXgeQEdz9fvDDkNKyHnbHRFtOr7/LcfgBcmct7t/ET+HaCTqfh06OzoAxrkN/IfjJBVe+g==",
-          "dev": true,
           "requires": {
             "abort-controller": "^3.0.0",
             "buffer": "^6.0.3",
@@ -26205,14 +26065,12 @@
         "safe-buffer": {
           "version": "5.2.1",
           "resolved": "https://registry.npmjs.org/safe-buffer/-/safe-buffer-5.2.1.tgz",
-          "integrity": "sha512-rp3So07KcdmmKbGvgaNxQSJr7bGVSVk5S9Eq1F+ppbRo70+YeaDxkw5Dd8NPN+GD6bjnYm2VuPuCXmpuYvmCXQ==",
-          "dev": true
+          "integrity": "sha512-rp3So07KcdmmKbGvgaNxQSJr7bGVSVk5S9Eq1F+ppbRo70+YeaDxkw5Dd8NPN+GD6bjnYm2VuPuCXmpuYvmCXQ=="
         },
         "string_decoder": {
           "version": "1.3.0",
           "resolved": "https://registry.npmjs.org/string_decoder/-/string_decoder-1.3.0.tgz",
           "integrity": "sha512-hkRX8U1WjJFd8LsDJ2yQ/wWWxaopEsABU1XfkM8A+j0+85JAGppt16cr1Whg6KIbb4okU6Mql6BOj+uup/wKeA==",
-          "dev": true,
           "requires": {
             "safe-buffer": "~5.2.0"
           }
diff --git a/package.json b/package.json
index 00beb1d47..11cd0278f 100644
--- a/package.json
+++ b/package.json
@@ -871,11 +871,13 @@
     "@deephaven-enterprise/auth-nodejs": "^1.20240723.124-beta",
     "@deephaven-enterprise/query-utils": "^1.20240723.124-beta",
     "@deephaven/jsapi-nodejs": "^0.104.0",
+    "archiver": "^7.0.1",
     "nanoid": "^5.0.7"
   },
   "devDependencies": {
     "@deephaven-enterprise/jsapi-types": "^1.20240723.124-beta",
     "@deephaven/jsapi-types": "^1.0.0-dev0.37.3",
+    "@types/archiver": "^6.0.3",
     "@types/node": "22.5.4",
     "@types/vscode": "^1.91.0",
     "@types/ws": "^8.5.10",
diff --git a/src/controllers/ExtensionController.ts b/src/controllers/ExtensionController.ts
index cd5fc2bc8..06d96405f 100644
--- a/src/controllers/ExtensionController.ts
+++ b/src/controllers/ExtensionController.ts
@@ -1,4 +1,5 @@
 import * as vscode from 'vscode';
+import * as os from 'os';
 import type { dh as DhcType } from '@deephaven/jsapi-types';
 import type { EnterpriseDhType as DheType } from '@deephaven-enterprise/jsapi-types';
 import {
@@ -32,10 +33,13 @@ import {
   getTempDir,
   isInstanceOf,
   isSupportedLanguageId,
+  LogFileHandler,
   Logger,
   OutputChannelWithHistory,
   sanitizeGRPCLogMessageArgs,
+  saveLogFiles,
   Toaster,
+  uniqueId,
 } from '../util';
 import {
   RunCommandCodeLensProvider,
@@ -79,6 +83,7 @@ import type {
   CoreUnauthenticatedClient,
   ConnectionState,
   WorkerURL,
+  UniqueID,
 } from '../types';
 import { ServerConnectionTreeDragAndDropController } from './ServerConnectionTreeDragAndDropController';
 import { ConnectionController } from './ConnectionController';
@@ -92,34 +97,38 @@ export class ExtensionController implements Disposable {
   constructor(context: vscode.ExtensionContext, configService: IConfigService) {
     this._context = context;
     this._config = configService;
+    this._instanceId = uniqueId(8);
+    this._version = this._context.extension.packageJSON.version;
+
+    const envInfo = {
+      /* eslint-disable @typescript-eslint/naming-convention */
+      'VS Code version': vscode.version,
+      'Deephaven Extension version': this._version,
+      'Deephaven Extension instanceId': this._instanceId,
+      'Electron version': process.versions.electron,
+      'Chromium version': process.versions.chrome,
+      'Node version': process.versions.node,
+      /* eslint-enable @typescript-eslint/naming-convention */
+      platform: os.platform(),
+      release: os.release(),
+      arch: os.arch(),
+      version: os.version(),
+      totalmem: os.totalmem(),
+      freemem: os.freemem(),
+      cpus: os.cpus(),
+      uptime: os.uptime(),
+    };
 
-    this.initializeDiagnostics();
-    this.initializeConfig();
-    this.initializeSecrets();
-    this.initializeCodeLenses();
-    this.initializeHoverProviders();
-    this.initializeMessaging();
-    this.initializeServerManager();
-    this.initializeTempDirectory();
-    this.initializeConnectionController();
-    this.initializePanelController();
-    this.initializePipServerController();
-    this.initializeUserLoginController();
-    this.initializeCommands();
-    this.initializeWebViews();
-    this.initializeServerUpdates();
-
-    this._context.subscriptions.push(NodeHttp2gRPCTransport);
-
-    const version = context.extension.packageJSON.version;
-    const message = `Deephaven extension ${version} activated`;
-
-    logger.info(message);
-    this._outputChannel?.appendLine(message);
+    this._envInfoText = Object.entries(envInfo)
+      .map(([key, value]) => `\t${key}: ${JSON.stringify(value)}`)
+      .join('\n');
   }
 
-  readonly _context: vscode.ExtensionContext;
-  readonly _config: IConfigService;
+  private readonly _context: vscode.ExtensionContext;
+  private readonly _config: IConfigService;
+  private readonly _instanceId: UniqueID;
+  private readonly _version: string;
+  private readonly _envInfoText: string;
 
   private _connectionController: ConnectionController | null = null;
   private _coreClientCache: URLMap<
@@ -132,6 +141,7 @@ export class ExtensionController implements Disposable {
     null;
   private _dheClientFactory: IDheClientFactory | null = null;
   private _dheServiceCache: IAsyncCacheService<URL, IDheService> | null = null;
+  private _logFileHandler: LogFileHandler | null = null;
   private _panelController: PanelController | null = null;
   private _panelService: IPanelService | null = null;
   private _pipServerController: PipServerController | null = null;
@@ -162,6 +172,38 @@ export class ExtensionController implements Disposable {
 
   async dispose(): Promise<void> {}
 
+  activate = (): void => {
+    this.initializeMessaging();
+
+    logger.info(`Activating Deephaven extension\n${this._envInfoText}`);
+
+    this.initializeDiagnostics();
+    this.initializeConfig();
+    this.initializeSecrets();
+    this.initializeCodeLenses();
+    this.initializeHoverProviders();
+    this.initializeServerManager();
+    this.initializeTempDirectory();
+    this.initializeConnectionController();
+    this.initializePanelController();
+    this.initializePipServerController();
+    this.initializeUserLoginController();
+    this.initializeCommands();
+    this.initializeWebViews();
+    this.initializeServerUpdates();
+
+    this._context.subscriptions.push(NodeHttp2gRPCTransport);
+
+    const message = `Activated Deephaven Extension.`;
+
+    logger.info(message);
+    this._outputChannel?.appendLine(message);
+  };
+
+  deactivate = (): void => {
+    logger.info(`Deactivating Deephaven extension`);
+  };
+
   /**
    * Initialize code lenses for running Deephaven code.
    */
@@ -321,6 +363,9 @@ export class ExtensionController implements Disposable {
     Logger.addConsoleHandler();
     Logger.addOutputChannelHandler(this._outputChannelDebug);
 
+    this._logFileHandler = new LogFileHandler(this._instanceId, this._context);
+    Logger.handlers.add(this._logFileHandler);
+
     const gRPCOutputChannelHandler = Logger.createOutputChannelHandler(
       this._outputChannelDebug
     );
@@ -332,6 +377,7 @@ export class ExtensionController implements Disposable {
     this._toaster = new Toaster();
 
     this._context.subscriptions.push(
+      this._logFileHandler,
       this._outputChannel,
       this._outputChannelDebug
     );
@@ -695,14 +741,19 @@ export class ExtensionController implements Disposable {
    * Handle download logs command
    */
   onDownloadLogs = async (): Promise<void> => {
+    assertDefined(this._logFileHandler, 'logFileHandler');
     assertDefined(this._outputChannelDebug, 'outputChannelDebug');
     assertDefined(this._toaster, 'toaster');
 
-    const uri = await this._outputChannelDebug.downloadHistoryToFile();
+    const uri = await saveLogFiles(this._logFileHandler.logDirectory);
 
     if (uri != null) {
       this._toaster.info(`Downloaded logs to ${uri.fsPath}`);
-      vscode.window.showTextDocument(uri);
+
+      await vscode.commands.executeCommand(
+        'revealFileInOS',
+        vscode.Uri.parse(uri.fsPath)
+      );
     }
   };
 
diff --git a/src/extension.ts b/src/extension.ts
index 14aef31b6..77acf5789 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -2,10 +2,15 @@ import * as vscode from 'vscode';
 import { ExtensionController } from './controllers';
 import { ConfigService } from './services';
 
-export function activate(context: vscode.ExtensionContext): void {
-  const controller = new ExtensionController(context, ConfigService);
+let controller: ExtensionController | undefined;
 
+export function activate(context: vscode.ExtensionContext): void {
+  controller = new ExtensionController(context, ConfigService);
   context.subscriptions.push(controller);
+
+  controller.activate();
 }
 
-export function deactivate(): void {}
+export function deactivate(): void {
+  controller?.deactivate();
+}
diff --git a/src/util/Logger.ts b/src/util/Logger.ts
index ab1c50a76..7f317f18b 100644
--- a/src/util/Logger.ts
+++ b/src/util/Logger.ts
@@ -1,4 +1,8 @@
 import * as vscode from 'vscode';
+import fs from 'node:fs';
+import path from 'node:path';
+import type { Disposable, UniqueID } from '../types';
+import { getFilePathDateToken } from './dataUtils';
 
 export type LogLevel = 'error' | 'warn' | 'info' | 'debug' | 'debug2';
 
@@ -6,6 +10,65 @@ export type LogLevelHandler = (label: string, ...args: unknown[]) => void;
 
 export type LogHandler = Record<LogLevel, LogLevelHandler>;
 
+/**
+ * Log handler that writes logs to a file.
+ */
+export class LogFileHandler implements LogHandler, Disposable {
+  constructor(extensionInstanceId: UniqueID, context: vscode.ExtensionContext) {
+    // VS Code specifies the log directory but doesn't create it
+    fs.mkdirSync(context.logUri.fsPath, { recursive: true });
+
+    this._extensionInstanceId = extensionInstanceId;
+    this.logDirectory = context.logUri.fsPath;
+  }
+
+  private readonly _extensionInstanceId: UniqueID;
+  private _lastLogBucket: string | null = null;
+  private _logWriter: fs.WriteStream | null = null;
+
+  readonly logDirectory: string;
+
+  private _getLogFilePath = (isoDateStr: string): string => {
+    const dateToken = getFilePathDateToken(isoDateStr);
+
+    const logFileName = `deephaven-vscode_${dateToken}_${this._extensionInstanceId}.log`;
+    return path.join(this.logDirectory, logFileName);
+  };
+
+  private _write = (
+    level: LogLevel,
+    label: string,
+    ...args: unknown[]
+  ): void => {
+    const now = new Date().toISOString();
+    const hourBucket = now.substring(0, 13);
+
+    // Initialize log writer or update it if the hour bucket has changed
+    if (this._logWriter == null || this._lastLogBucket !== hourBucket) {
+      this._logWriter?.end();
+      this._lastLogBucket = hourBucket;
+
+      const logFilePath = this._getLogFilePath(now);
+      this._logWriter = fs.createWriteStream(logFilePath);
+    }
+
+    this._logWriter.write(
+      `[${now}] ${label} ${level.toUpperCase()}: ${args.map(Logger.stringifyArg).join(' ')}\n`
+    );
+  };
+
+  error = this._write.bind(this, 'error');
+  warn = this._write.bind(this, 'warn');
+  info = this._write.bind(this, 'info');
+  debug = this._write.bind(this, 'debug');
+  debug2 = this._write.bind(this, 'debug2');
+
+  dispose = async (): Promise<void> => {
+    this._logWriter?.end();
+    this._logWriter = null;
+  };
+}
+
 /**
  * Simple logger delegate that can be used to log messages to a set of handlers.
  * Messages will include a label for scoping log messages.
diff --git a/src/util/dataUtils.ts b/src/util/dataUtils.ts
index 826f8f911..ff526f317 100644
--- a/src/util/dataUtils.ts
+++ b/src/util/dataUtils.ts
@@ -1,5 +1,21 @@
 import type { NonEmptyArray } from '../types';
 
+/**
+ * Returns a date string formatted for use in a file path.
+ * The format is YYYYMMDDTHHMMSSZ.
+ * @param dateOrIsoString A Date object or an ISO 8601 date string.
+ * @returns A string formatted for use in a file path.
+ */
+export function getFilePathDateToken(
+  dateOrIsoString: Date | string = new Date()
+): string {
+  if (dateOrIsoString instanceof Date) {
+    dateOrIsoString = dateOrIsoString.toISOString();
+  }
+
+  return `${dateOrIsoString.substring(0, 19).replace(/[:-]/g, '')}Z`;
+}
+
 /**
  * Type guard to determine if an object has a property.
  * @param obj The object to check.
diff --git a/src/util/idUtils.ts b/src/util/idUtils.ts
index 31da7ae3f..fb184b5b1 100644
--- a/src/util/idUtils.ts
+++ b/src/util/idUtils.ts
@@ -1,11 +1,15 @@
-import { nanoid } from 'nanoid';
+import { customAlphabet, urlAlphabet } from 'nanoid';
 import type { UniqueID } from '../types';
 
+// The default nanoid alphabet includes `_`. Using custom alphabet without it
+// to make ids group better in `_` delimited strings.
+const nanoidCustom = customAlphabet(urlAlphabet.replace('_', ''), 21);
+
 /**
  * Generate a unique id.
  * @param size The size of the id to generate. Defaults to 21 since that is what
  * nanoid uses as its default.
  */
 export function uniqueId(size: number = 21): UniqueID {
-  return nanoid(size) as UniqueID;
+  return nanoidCustom(size) as UniqueID;
 }
diff --git a/src/util/uiUtils.ts b/src/util/uiUtils.ts
index ad6189530..e89f02b71 100644
--- a/src/util/uiUtils.ts
+++ b/src/util/uiUtils.ts
@@ -1,5 +1,13 @@
 import * as vscode from 'vscode';
 import * as fs from 'node:fs';
+import * as path from 'node:path';
+import archiver from 'archiver';
+import type {
+  KeyPairCredentials,
+  OperateAsUsername,
+  PasswordCredentials,
+  Username,
+} from '@deephaven-enterprise/auth-nodejs';
 import {
   SELECT_CONNECTION_COMMAND,
   STATUS_BAR_CONNECTING_TEXT,
@@ -19,14 +27,11 @@ import type {
   DependencyName,
   DependencyVersion,
 } from '../types';
-import { sortByStringProp } from './dataUtils';
+import { getFilePathDateToken, sortByStringProp } from './dataUtils';
 import { assertDefined } from './assertUtil';
-import type {
-  KeyPairCredentials,
-  OperateAsUsername,
-  PasswordCredentials,
-  Username,
-} from '@deephaven-enterprise/auth-nodejs';
+import { Logger } from './Logger';
+
+const logger = new Logger('uiUtils');
 
 export interface ConnectionOption {
   type: ConnectionType;
@@ -472,24 +477,111 @@ export function promptForOperateAs(
 }
 
 /**
- * Save a map of dependency name / versions to a `requirements.txt` file.
- * @param dependencies The map of dependency names / versions to save.
- * @returns Promise that resolves when the file is saved.
+ * Open a save file dialog for a given file name and filters. Defaults to
+ * workspace folder if it can be determined. Otherwise will default to whatever
+ * VS Code determines for the environment.
+ * @param fileName The file name to use as the default.
+ * @param filters A set of file filters that are used by the save file dialog.
+ * Each key is a human-readable name for the filter and the value is an array of
+ * file extensions. For example:
+ * {
+ *   'Images': ['png', 'jpg'],
+ *   'TypeScript': ['ts', 'tsx']
+ * }
+ * @returns The selected file URI or undefined if cancelled.
  */
-export async function saveRequirementsTxt(
-  dependencies: Map<DependencyName, DependencyVersion>
-): Promise<void> {
+export async function showWorkspaceSaveDialog(
+  fileName: string,
+  filters: vscode.SaveDialogOptions['filters']
+): Promise<vscode.Uri | undefined> {
   const wkspFolder = getWorkspaceFolder();
 
   const defaultUri =
     wkspFolder == null
-      ? vscode.Uri.file('requirements.txt')
-      : vscode.Uri.joinPath(wkspFolder.uri, 'requirements.txt');
+      ? vscode.Uri.file(fileName)
+      : vscode.Uri.joinPath(wkspFolder.uri, fileName);
 
-  const uri = await vscode.window.showSaveDialog({
+  return vscode.window.showSaveDialog({
     defaultUri,
+    filters,
+  });
+}
+
+/**
+ * Zip and save logs for Deephaven VS Code extension.
+ * @param logDirectory The directory containing the log files to save.
+ * @returns The URI for the saved .zip file
+ */
+export async function saveLogFiles(
+  logDirectory: string
+): Promise<vscode.Uri | null> {
+  const uri = await showWorkspaceSaveDialog(
+    `deephaven-vscode_${getFilePathDateToken()}.zip`,
+    {
+      // eslint-disable-next-line @typescript-eslint/naming-convention
+      'Log Files': ['zip'],
+    }
+  );
+
+  if (uri == null) {
+    return null;
+  }
+
+  logger.debug(`Saving log files from '${logDirectory}' to '${uri.fsPath}'.`);
+
+  const writeStream = fs.createWriteStream(uri.fsPath);
+  const archive = archiver('zip', {
+    zlib: { level: 9 }, // Sets the compression level.
+  });
+
+  const promise = new Promise<vscode.Uri>((resolve, reject) => {
+    writeStream.on('close', function () {
+      logger.debug(archive.pointer() + ' total bytes');
+      logger.debug(
+        'archiver has been finalized and the output file descriptor has closed.'
+      );
+      resolve(uri);
+    });
+
+    archive.on('warning', err => {
+      if (err.code === 'ENOENT') {
+        logger.warn(err);
+      } else {
+        reject(err);
+      }
+    });
+
+    archive.on('error', err => {
+      reject(err);
+    });
+  });
+
+  archive.pipe(writeStream);
+
+  // Include the `exthost.log` which contains entries for all extensions
+  archive.file(path.join(path.dirname(logDirectory), 'exthost.log'), {
+    name: 'exthost.log',
+  });
+
+  // Include Deephaven extension logs
+  archive.directory(logDirectory, false);
+
+  archive.finalize();
+
+  return promise;
+}
+
+/**
+ * Save a map of dependency name / versions to a `requirements.txt` file.
+ * @param dependencies The map of dependency names / versions to save.
+ * @returns Promise that resolves when the file is saved.
+ */
+export async function saveRequirementsTxt(
+  dependencies: Map<DependencyName, DependencyVersion>
+): Promise<void> {
+  const uri = await showWorkspaceSaveDialog('requirements.txt', {
     // eslint-disable-next-line @typescript-eslint/naming-convention
-    filters: { Requirements: ['txt'] },
+    Requirements: ['txt'],
   });
 
   if (uri == null) {