diff --git a/.npmrc b/.npmrc
index 2c7c6c1b58489..b07eade64d573 100644
--- a/.npmrc
+++ b/.npmrc
@@ -1,6 +1,6 @@
 disturl="https://electronjs.org/headers"
-target="39.6.1"
-ms_build_id="13369494"
+target="39.6.0"
+ms_build_id="13330601"
 runtime="electron"
 ignore-scripts=false
 build_from_source="true"
diff --git a/build/azure-pipelines/common/sanity-tests.yml b/build/azure-pipelines/common/sanity-tests.yml
index 3606777f9a375..4e47f4672a002 100644
--- a/build/azure-pipelines/common/sanity-tests.yml
+++ b/build/azure-pipelines/common/sanity-tests.yml
@@ -29,9 +29,19 @@ jobs:
       name: ${{ parameters.poolName }}
       os: ${{ parameters.os }}
     timeoutInMinutes: 30
+    templateContext:
+      outputs:
+        - output: pipelineArtifact
+          targetPath: $(SCREENSHOTS_DIR)
+          artifactName: screenshots-${{ parameters.name }}
+          displayName: Publish Screenshots
+          condition: succeededOrFailed()
+          continueOnError: true
+          sbomEnabled: false
     variables:
       TEST_DIR: $(Build.SourcesDirectory)/test/sanity
       LOG_FILE: $(TEST_DIR)/results.xml
+      SCREENSHOTS_DIR: $(TEST_DIR)/screenshots
       DOCKER_CACHE_DIR: $(Pipeline.Workspace)/docker-cache
       DOCKER_CACHE_FILE: $(DOCKER_CACHE_DIR)/${{ parameters.container }}.tar
     steps:
@@ -41,6 +51,14 @@ jobs:
         sparseCheckoutDirectories: test/sanity .nvmrc
         displayName: Checkout test/sanity
 
+      - ${{ if eq(parameters.os, 'windows') }}:
+        - script: mkdir "$(SCREENSHOTS_DIR)"
+          displayName: Create Screenshots Directory
+
+      - ${{ else }}:
+        - bash: mkdir -p "$(SCREENSHOTS_DIR)"
+          displayName: Create Screenshots Directory
+
       - ${{ if and(eq(parameters.os, 'windows'), eq(parameters.arch, 'arm64')) }}:
         - script: |
             @echo off
@@ -101,19 +119,19 @@ jobs:
 
       # Windows
       - ${{ if eq(parameters.os, 'windows') }}:
-        - script: $(TEST_DIR)/scripts/run-win32.cmd -c $(BUILD_COMMIT) -q $(BUILD_QUALITY) -t $(LOG_FILE) -v ${{ parameters.args }}
+        - script: $(TEST_DIR)/scripts/run-win32.cmd -c $(BUILD_COMMIT) -q $(BUILD_QUALITY) -t $(LOG_FILE) -s $(SCREENSHOTS_DIR) -v ${{ parameters.args }}
           workingDirectory: $(TEST_DIR)
           displayName: Run Sanity Tests
 
       # macOS
       - ${{ if eq(parameters.os, 'macOS') }}:
-        - bash: $(TEST_DIR)/scripts/run-macOS.sh -c $(BUILD_COMMIT) -q $(BUILD_QUALITY) -t $(LOG_FILE) -v ${{ parameters.args }}
+        - bash: $(TEST_DIR)/scripts/run-macOS.sh -c $(BUILD_COMMIT) -q $(BUILD_QUALITY) -t $(LOG_FILE) -s $(SCREENSHOTS_DIR) -v ${{ parameters.args }}
           workingDirectory: $(TEST_DIR)
           displayName: Run Sanity Tests
 
       # Native Linux host
       - ${{ if and(eq(parameters.container, ''), eq(parameters.os, 'linux')) }}:
-        - bash: $(TEST_DIR)/scripts/run-ubuntu.sh -c $(BUILD_COMMIT) -q $(BUILD_QUALITY) -t $(LOG_FILE) -v ${{ parameters.args }}
+        - bash: $(TEST_DIR)/scripts/run-ubuntu.sh -c $(BUILD_COMMIT) -q $(BUILD_QUALITY) -t $(LOG_FILE) -s $(SCREENSHOTS_DIR) -v ${{ parameters.args }}
           workingDirectory: $(TEST_DIR)
           displayName: Run Sanity Tests
 
@@ -141,6 +159,7 @@ jobs:
               --quality "$(BUILD_QUALITY)" \
               --commit "$(BUILD_COMMIT)" \
               --test-results "/root/results.xml" \
+              --screenshots-dir "/root/screenshots" \
               --verbose \
               ${{ parameters.args }}
           workingDirectory: $(TEST_DIR)
diff --git a/build/checksums/electron.txt b/build/checksums/electron.txt
index 90e662c384deb..3df57a48a97d2 100644
--- a/build/checksums/electron.txt
+++ b/build/checksums/electron.txt
@@ -1,75 +1,75 @@
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-d64a85751e3b779ce9d4e88ab0e25db4970594f7c2b4995a21d5bfce8d6b63f0 *chromedriver-v39.6.1-linux-arm64.zip
-83e938f9b5c19785d32f510a4ef5eab9ac6e63d40944b0e759a5f85867a02b72 *chromedriver-v39.6.1-linux-armv7l.zip
-b1cd220f1c71edd4aeb57910cbf63bdf8862c62a1c3270ae7af5a4bd2098fe6f *chromedriver-v39.6.1-linux-x64.zip
-c63e4ea9a0bdb883d2a6369919262a7ff3f9b432dfdcd32c827debbabfa6e8e4 *chromedriver-v39.6.1-mas-arm64.zip
-d073ed5147b5adf3aefc88c5ee24c0998a8930849d10f886a1e553b99ed001b9 *chromedriver-v39.6.1-mas-x64.zip
-7d475b4bbddb9a6b2ab1fd7793cbe5fd2a3b3e8ee291b804ff1773d3a6432482 *chromedriver-v39.6.1-win32-arm64.zip
-ff7175e1953a604a3d033eac76c0be6c0c6cadce014459c23186b4ce35ee632b *chromedriver-v39.6.1-win32-ia32.zip
-2c3591abbc4a11ea9508d02eb9e9152eba7ef693746696723239cac8db4faac1 *chromedriver-v39.6.1-win32-x64.zip
-c97d31018c4f3229555607f71e14ddf44ecf78b684055dce548ae5117b4fd284 *electron-api.json
-9777c57ec393cb9961500f645166b3f05a9e1ddd8472474c3c6ae9f8224cc029 *electron-v39.6.1-darwin-arm64-dsym-snapshot.zip
-005d1a2b75c7e022eda48ecb5b8026e7556b9e12ad6bbd3de39b555a299edbd9 *electron-v39.6.1-darwin-arm64-dsym.zip
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+81ae98e064485f8c6c69cd6c875ee72666c0cc801a8549620d382c2d0cea3b5c *mksnapshot-v39.6.0-mas-x64.zip
+2e44f75df797922e7c8bad61a1b41fed14b070a54257a6a751892b2b8b9dfe29 *mksnapshot-v39.6.0-win32-arm64-x64.zip
+fb5d73a8bf4b8db80f61b7073aa8458b5c46cce5c2a4b23591e851c6fcbd0144 *mksnapshot-v39.6.0-win32-ia32.zip
+118ae88dbcd6b260cfa370e46ccfb0ab00af5efbf59495aaeea56a2831f604b2 *mksnapshot-v39.6.0-win32-x64.zip
diff --git a/build/gulpfile.vscode.win32.ts b/build/gulpfile.vscode.win32.ts
index 0f81323c98db2..1f525cff35a90 100644
--- a/build/gulpfile.vscode.win32.ts
+++ b/build/gulpfile.vscode.win32.ts
@@ -113,7 +113,7 @@ function buildWin32Setup(arch: string, target: string): task.CallbackTask {
 			Quality: quality
 		};
 
-		const isInsiderOrExploration = quality === 'insider' || quality === 'exploration';
+		const isInsiderOrExploration = false;
 		const embedded = isInsiderOrExploration
 			? (product as typeof product & { embedded?: EmbeddedProductInfo }).embedded
 			: undefined;
diff --git a/cgmanifest.json b/cgmanifest.json
index 45f578c1b9767..21554434500a7 100644
--- a/cgmanifest.json
+++ b/cgmanifest.json
@@ -529,13 +529,13 @@
 				"git": {
 					"name": "electron",
 					"repositoryUrl": "https://github.com/electron/electron",
-					"commitHash": "2ffb9e1e05c55975112ff6b23037af0eeda79142",
-					"tag": "39.6.1"
+					"commitHash": "a229dbf7a56336b847b34dfff1bac79afc311eee",
+					"tag": "39.6.0"
 				}
 			},
 			"isOnlyProductionDependency": true,
 			"license": "MIT",
-			"version": "39.6.1"
+			"version": "39.6.0"
 		},
 		{
 			"component": {
diff --git a/extensions/github-authentication/media/index.html b/extensions/github-authentication/media/index.html
index 3292e2a08fc9f..2df45293528fa 100644
--- a/extensions/github-authentication/media/index.html
+++ b/extensions/github-authentication/media/index.html
@@ -30,9 +30,17 @@ <h1 class="title">Launching <span class="app-name"></span></h1>
 	</div>
 	<script>
 		const urlParams = new URLSearchParams(window.location.search);
+
 		const appName = urlParams.get('app_name');
 		document.querySelectorAll('.app-name').forEach(e => e.innerText = appName);
 
+		if (urlParams.get('app_is_sessions') === 'true') {
+			const iconImg = document.querySelector('.icon-container img');
+			if (iconImg) {
+				iconImg.src = 'sessions-icon.svg';
+			}
+		}
+
 		// if name contains 'insiders', update filter CSS variables
 		if (appName.toLowerCase().includes('insiders')) {
 			document.documentElement.style.setProperty('--vscode-filter-0', 'var(--vscode-insiders-filter-0)');
diff --git a/extensions/github-authentication/media/sessions-icon.svg b/extensions/github-authentication/media/sessions-icon.svg
new file mode 100644
index 0000000000000..d1eb57cf32618
--- /dev/null
+++ b/extensions/github-authentication/media/sessions-icon.svg
@@ -0,0 +1,24 @@
+<svg width="1024" height="1024" viewBox="0 0 1024 1024" fill="none" xmlns="http://www.w3.org/2000/svg">
+<path d="M64 302.719C64 333.652 80.64 361.599 106.667 376.532L469.333 585.812V930.772C469.333 945.919 461.227 959.999 448 967.679C434.773 975.359 418.56 975.359 405.333 967.679L85.3333 782.932C72.1067 775.252 64 761.172 64 746.025V302.719Z" fill="url(#paint0_linear_608_6009)"/>
+<path d="M448 56.3225C461.227 64.0025 469.333 78.0825 469.333 93.2292V585.816L106.667 376.536C80.64 361.603 64 333.656 64 302.723C64 272.216 80.2133 244.056 106.667 228.696L405.333 56.3225C418.56 48.6425 434.773 48.6425 448 56.3225Z" fill="url(#paint1_linear_608_6009)"/>
+<path d="M618.667 56.3225L938.667 241.069C951.893 248.749 960 262.829 960 277.976V721.283C960 690.349 943.36 662.403 917.333 647.469L554.667 437.976V93.2292C554.667 78.0825 562.773 64.0025 576 56.3225C589.227 48.6425 605.44 48.6425 618.667 56.3225Z" fill="url(#paint2_linear_608_6009)"/>
+<path d="M554.667 437.974L917.333 647.467C943.36 662.401 960 690.347 960 721.281C960 752.214 943.787 779.947 917.333 795.307L618.667 967.681C605.44 975.361 589.227 975.361 576 967.681C562.773 960.001 554.667 945.921 554.667 930.774V437.974Z" fill="url(#paint3_linear_608_6009)"/>
+<defs>
+<linearGradient id="paint0_linear_608_6009" x1="469.333" y1="586.667" x2="64" y2="586.667" gradientUnits="userSpaceOnUse">
+<stop stop-color="#1797D9"/>
+<stop offset="1" stop-color="#087CBF"/>
+</linearGradient>
+<linearGradient id="paint1_linear_608_6009" x1="181.333" y1="405.333" x2="394.667" y2="53.3333" gradientUnits="userSpaceOnUse">
+<stop stop-color="#005B9E"/>
+<stop offset="1" stop-color="#087CBF"/>
+</linearGradient>
+<linearGradient id="paint2_linear_608_6009" x1="970.667" y1="166.975" x2="554.667" y2="166.975" gradientUnits="userSpaceOnUse">
+<stop offset="0.0211942" stop-color="#26B2F3"/>
+<stop offset="1" stop-color="#3AC6FF"/>
+</linearGradient>
+<linearGradient id="paint3_linear_608_6009" x1="570.2" y1="973.443" x2="810.667" y2="581.333" gradientUnits="userSpaceOnUse">
+<stop stop-color="#1EA5E6"/>
+<stop offset="1" stop-color="#087CBF"/>
+</linearGradient>
+</defs>
+</svg>
diff --git a/extensions/github-authentication/package.json b/extensions/github-authentication/package.json
index 91f2d1b57dbcb..e343bb19900ac 100644
--- a/extensions/github-authentication/package.json
+++ b/extensions/github-authentication/package.json
@@ -19,7 +19,8 @@
   ],
   "enabledApiProposals": [
     "authIssuers",
-    "authProviderSpecific"
+    "authProviderSpecific",
+    "agentSessionsWorkspace"
   ],
   "activationEvents": [],
   "capabilities": {
diff --git a/extensions/github-authentication/src/common/env.ts b/extensions/github-authentication/src/common/env.ts
index ebc474936aa40..5456fb864ee4c 100644
--- a/extensions/github-authentication/src/common/env.ts
+++ b/extensions/github-authentication/src/common/env.ts
@@ -8,12 +8,15 @@ import { AuthProviderType } from '../github';
 const VALID_DESKTOP_CALLBACK_SCHEMES = [
 	'vscode',
 	'vscode-insiders',
+	'vscode-exploration',
+	'vscode-sessions',
+	'vscode-sessions-insiders',
+	'vscode-sessions-exploration',
 	// On Windows, some browsers don't seem to redirect back to OSS properly.
 	// As a result, you get stuck in the auth flow. We exclude this from the
 	// list until we can figure out a way to fix this behavior in browsers.
 	// 'code-oss',
 	'vscode-wsl',
-	'vscode-exploration'
 ];
 
 export function isSupportedClient(uri: Uri): boolean {
diff --git a/extensions/github-authentication/src/node/authServer.ts b/extensions/github-authentication/src/node/authServer.ts
index 45dca93e2d0a6..76b7fe61084d0 100644
--- a/extensions/github-authentication/src/node/authServer.ts
+++ b/extensions/github-authentication/src/node/authServer.ts
@@ -7,7 +7,7 @@ import { URL } from 'url';
 import * as fs from 'fs';
 import * as path from 'path';
 import { randomBytes } from 'crypto';
-import { env } from 'vscode';
+import { env, workspace } from 'vscode';
 
 function sendFile(res: http.ServerResponse, filepath: string) {
 	const isSvg = filepath.endsWith('.svg');
@@ -99,13 +99,14 @@ export class LoopbackAuthServer implements ILoopbackServer {
 		this._resultPromise = new Promise<IOAuthResult>((resolve, reject) => deferred = { resolve, reject });
 
 		const appNameQueryParam = `&app_name=${encodeURIComponent(env.appName)}`;
+		const appIsSessionsQueryParam = workspace.isAgentSessionsWorkspace ? '&app_is_sessions=true' : '';
 		this._server = http.createServer((req, res) => {
 			const reqUrl = new URL(req.url!, `http://${req.headers.host}`);
 			switch (reqUrl.pathname) {
 				case '/signin': {
 					const receivedNonce = (reqUrl.searchParams.get('nonce') ?? '').replace(/ /g, '+');
 					if (receivedNonce !== this.nonce) {
-						res.writeHead(302, { location: `/?error=${encodeURIComponent('Nonce does not match.')}${appNameQueryParam}` });
+						res.writeHead(302, { location: `/?error=${encodeURIComponent('Nonce does not match.')}${appNameQueryParam}${appIsSessionsQueryParam}` });
 						res.end();
 					}
 					res.writeHead(302, { location: this._startingRedirect.toString() });
@@ -122,20 +123,20 @@ export class LoopbackAuthServer implements ILoopbackServer {
 						return;
 					}
 					if (this.state !== state) {
-						res.writeHead(302, { location: `/?error=${encodeURIComponent('State does not match.')}${appNameQueryParam}` });
+						res.writeHead(302, { location: `/?error=${encodeURIComponent('State does not match.')}${appNameQueryParam}${appIsSessionsQueryParam}` });
 						res.end();
 						throw new Error('State does not match.');
 					}
 					if (this.nonce !== nonce) {
-						res.writeHead(302, { location: `/?error=${encodeURIComponent('Nonce does not match.')}${appNameQueryParam}` });
+						res.writeHead(302, { location: `/?error=${encodeURIComponent('Nonce does not match.')}${appNameQueryParam}${appIsSessionsQueryParam}` });
 						res.end();
 						throw new Error('Nonce does not match.');
 					}
 					deferred.resolve({ code, state });
 					if (isPortable) {
-						res.writeHead(302, { location: `/?app_name=${encodeURIComponent(env.appName)}` });
+						res.writeHead(302, { location: `/?app_name=${encodeURIComponent(env.appName)}${appIsSessionsQueryParam}` });
 					} else {
-						res.writeHead(302, { location: `/?redirect_uri=${encodeURIComponent(callbackUri)}${appNameQueryParam}` });
+						res.writeHead(302, { location: `/?redirect_uri=${encodeURIComponent(callbackUri)}${appNameQueryParam}${appIsSessionsQueryParam}` });
 					}
 					res.end();
 					break;
diff --git a/extensions/github-authentication/tsconfig.json b/extensions/github-authentication/tsconfig.json
index df8791cdebcd4..eac554232a0a5 100644
--- a/extensions/github-authentication/tsconfig.json
+++ b/extensions/github-authentication/tsconfig.json
@@ -14,6 +14,7 @@
 		"src/**/*",
 		"../../src/vscode-dts/vscode.d.ts",
 		"../../src/vscode-dts/vscode.proposed.authIssuers.d.ts",
-		"../../src/vscode-dts/vscode.proposed.authProviderSpecific.d.ts"
+		"../../src/vscode-dts/vscode.proposed.authProviderSpecific.d.ts",
+		"../../src/vscode-dts/vscode.proposed.agentSessionsWorkspace.d.ts"
 	]
 }
diff --git a/extensions/github/package.nls.json b/extensions/github/package.nls.json
index 4acc8acabcbab..04497595eb6d2 100644
--- a/extensions/github/package.nls.json
+++ b/extensions/github/package.nls.json
@@ -5,8 +5,8 @@
 	"command.publish": "Publish to GitHub",
 	"command.openOnGitHub": "Open on GitHub",
 	"command.openOnVscodeDev": "Open in vscode.dev",
-	"command.createPullRequest": "Create Pull Request",
-	"command.openPullRequest": "Open Pull Request",
+	"command.createPullRequest": "Create PR",
+	"command.openPullRequest": "Open PR",
 	"config.branchProtection": "Controls whether to query repository rules for GitHub repositories",
 	"config.gitAuthentication": "Controls whether to enable automatic GitHub authentication for git commands within VS Code.",
 	"config.gitProtocol": "Controls which protocol is used to clone a GitHub repository",
diff --git a/extensions/microsoft-authentication/src/common/env.ts b/extensions/microsoft-authentication/src/common/env.ts
index 9460a27d2fea9..b63c94195a9e9 100644
--- a/extensions/microsoft-authentication/src/common/env.ts
+++ b/extensions/microsoft-authentication/src/common/env.ts
@@ -9,12 +9,15 @@ export const DEFAULT_REDIRECT_URI = 'https://vscode.dev/redirect';
 const VALID_DESKTOP_CALLBACK_SCHEMES = [
 	'vscode',
 	'vscode-insiders',
+	'vscode-exploration',
+	'vscode-sessions',
+	'vscode-sessions-insiders',
+	'vscode-sessions-exploration',
 	// On Windows, some browsers don't seem to redirect back to OSS properly.
 	// As a result, you get stuck in the auth flow. We exclude this from the
 	// list until we can figure out a way to fix this behavior in browsers.
 	// 'code-oss',
 	'vscode-wsl',
-	'vscode-exploration'
 ];
 
 export function isSupportedClient(uri: Uri): boolean {
diff --git a/extensions/theme-2026/themes/2026-light.json b/extensions/theme-2026/themes/2026-light.json
index f11ffef290574..c743617242634 100644
--- a/extensions/theme-2026/themes/2026-light.json
+++ b/extensions/theme-2026/themes/2026-light.json
@@ -11,7 +11,7 @@
 		"icon.foreground": "#606060",
 		"focusBorder": "#0069CCFF",
 		"textBlockQuote.background": "#EAEAEA",
-		"textBlockQuote.border": "#F2F3F4FF",
+		"textBlockQuote.border": "#F0F1F2FF",
 		"textCodeBlock.background": "#EAEAEA",
 		"textLink.foreground": "#0069CC",
 		"textLink.activeForeground": "#0069CC",
@@ -38,7 +38,7 @@
 		"input.placeholderForeground": "#999999",
 		"inputOption.activeBackground": "#0069CC26",
 		"inputOption.activeForeground": "#202020",
-		"inputOption.activeBorder": "#F2F3F4FF",
+		"inputOption.activeBorder": "#F0F1F2FF",
 		"inputValidation.infoBackground": "#E6F2FA",
 		"inputValidation.infoBorder": "#0069CC",
 		"inputValidation.infoForeground": "#202020",
@@ -79,7 +79,7 @@
 		"activityBar.background": "#FAFAFD",
 		"activityBar.foreground": "#202020",
 		"activityBar.inactiveForeground": "#606060",
-		"activityBar.border": "#F2F3F4FF",
+		"activityBar.border": "#F0F1F2FF",
 		"activityBar.activeBorder": "#000000",
 		"activityBar.activeFocusBorder": "#0069CCFF",
 		"activityBarBadge.background": "#0069CC",
@@ -87,16 +87,16 @@
 		"activityBarTop.activeBorder": "#000000",
 		"sideBar.background": "#FAFAFD",
 		"sideBar.foreground": "#202020",
-		"sideBar.border": "#F2F3F4FF",
+		"sideBar.border": "#F0F1F2FF",
 		"sideBarTitle.foreground": "#202020",
 		"sideBarSectionHeader.background": "#FAFAFD",
 		"sideBarSectionHeader.foreground": "#202020",
-		"sideBarSectionHeader.border": "#F2F3F4FF",
+		"sideBarSectionHeader.border": "#F0F1F2FF",
 		"titleBar.activeBackground": "#FAFAFD",
 		"titleBar.activeForeground": "#606060",
 		"titleBar.inactiveBackground": "#FAFAFD",
 		"titleBar.inactiveForeground": "#606060",
-		"titleBar.border": "#F2F3F4FF",
+		"titleBar.border": "#F0F1F2FF",
 		"menubar.selectionBackground": "#EAEAEA",
 		"menubar.selectionForeground": "#202020",
 		"menu.background": "#FAFAFD",
@@ -104,7 +104,7 @@
 		"menu.selectionBackground": "#0069CC1A",
 		"menu.selectionForeground": "#202020",
 		"menu.separatorBackground": "#EEEEF1",
-		"menu.border": "#F2F3F4FF",
+		"menu.border": "#F0F1F2FF",
 		"commandCenter.foreground": "#202020",
 		"commandCenter.activeForeground": "#202020",
 		"commandCenter.background": "#FAFAFD",
@@ -133,7 +133,7 @@
 		"editorRuler.foreground": "#F7F7F7",
 		"editorCodeLens.foreground": "#606060",
 		"editorBracketMatch.background": "#0069CC40",
-		"editorBracketMatch.border": "#F2F3F4FF",
+		"editorBracketMatch.border": "#F0F1F2FF",
 		"editorWidget.background": "#F0F0F3",
 		"editorWidget.border": "#EEEEF1",
 		"editorWidget.foreground": "#202020",
@@ -160,7 +160,7 @@
 		"editorGutter.deletedBackground": "#ad0707",
 		"diffEditor.insertedTextBackground": "#587c0c26",
 		"diffEditor.removedTextBackground": "#ad070726",
-		"editorOverviewRuler.border": "#F2F3F4FF",
+		"editorOverviewRuler.border": "#F0F1F2FF",
 		"editorOverviewRuler.findMatchForeground": "#0069CC99",
 		"editorOverviewRuler.modifiedForeground": "#0069CC",
 		"editorOverviewRuler.addedForeground": "#587c0c",
@@ -169,13 +169,13 @@
 		"editorOverviewRuler.warningForeground": "#667309",
 		"editorGutter.background": "#FFFFFF",
 		"panel.background": "#FAFAFD",
-		"panel.border": "#F2F3F4FF",
+		"panel.border": "#F0F1F2FF",
 		"panelTitle.activeBorder": "#000000",
 		"panelTitle.activeForeground": "#202020",
 		"panelTitle.inactiveForeground": "#606060",
 		"statusBar.background": "#FAFAFD",
 		"statusBar.foreground": "#606060",
-		"statusBar.border": "#F2F3F4FF",
+		"statusBar.border": "#F0F1F2FF",
 		"statusBar.focusBorder": "#0069CCFF",
 		"statusBar.debuggingBackground": "#0069CC",
 		"statusBar.debuggingForeground": "#FFFFFF",
@@ -192,8 +192,8 @@
 		"tab.activeForeground": "#202020",
 		"tab.inactiveBackground": "#FAFAFD",
 		"tab.inactiveForeground": "#606060",
-		"tab.border": "#F2F3F4FF",
-		"tab.lastPinnedBorder": "#F2F3F4FF",
+		"tab.border": "#F0F1F2FF",
+		"tab.lastPinnedBorder": "#F0F1F2FF",
 		"tab.activeBorder": "#FAFAFD",
 		"tab.activeBorderTop": "#000000",
 		"tab.hoverBackground": "#DADADA4f",
@@ -203,19 +203,19 @@
 		"tab.unfocusedInactiveBackground": "#FAFAFD",
 		"tab.unfocusedInactiveForeground": "#BBBBBB",
 		"editorGroupHeader.tabsBackground": "#FAFAFD",
-		"editorGroupHeader.tabsBorder": "#F2F3F4FF",
+		"editorGroupHeader.tabsBorder": "#F0F1F2FF",
 		"breadcrumb.foreground": "#606060",
 		"breadcrumb.background": "#FFFFFF",
 		"breadcrumb.focusForeground": "#202020",
 		"breadcrumb.activeSelectionForeground": "#202020",
 		"breadcrumbPicker.background": "#F0F0F3",
-		"notificationCenter.border": "#F2F3F4FF",
+		"notificationCenter.border": "#F0F1F2FF",
 		"notificationCenterHeader.foreground": "#202020",
 		"notificationCenterHeader.background": "#FAFAFD",
-		"notificationToast.border": "#F2F3F4FF",
+		"notificationToast.border": "#F0F1F2FF",
 		"notifications.foreground": "#202020",
 		"notifications.background": "#FAFAFD",
-		"notifications.border": "#F2F3F4FF",
+		"notifications.border": "#F0F1F2FF",
 		"notificationLink.foreground": "#0069CC",
 		"notificationsWarningIcon.foreground": "#B69500",
 		"notificationsErrorIcon.foreground": "#ad0707",
@@ -250,7 +250,7 @@
 		"quickInput.border": "#D8D8D8",
 		"gauge.foreground": "#0069CC",
 		"gauge.background": "#0069CC40",
-		"gauge.border": "#F2F3F4FF",
+		"gauge.border": "#F0F1F2FF",
 		"gauge.warningForeground": "#B69500",
 		"gauge.warningBackground": "#B6950040",
 		"gauge.errorForeground": "#ad0707",
diff --git a/extensions/theme-2026/themes/styles.css b/extensions/theme-2026/themes/styles.css
index 45271d56843ea..af33a765e77aa 100644
--- a/extensions/theme-2026/themes/styles.css
+++ b/extensions/theme-2026/themes/styles.css
@@ -14,7 +14,6 @@
 	--shadow-xl: 0 0 20px rgba(0, 0, 0, 0.15);
 	--shadow-hover: 0 0 8px rgba(0, 0, 0, 0.12);
 	--shadow-sm-strong: 0 0 4px rgba(0, 0, 0, 0.18);
-	--shadow-button-active: inset 0 1px 2px rgba(0, 0, 0, 0.1);
 	--shadow-active-tab: 0 8px 12px rgba(0, 0, 0, 0.02);
 
 	/* Panel depth shadows cast onto the editor surface */
@@ -212,10 +211,6 @@
 	border-radius: var(--radius-lg);
 }
 
-.monaco-workbench.vs .interactive-session .chat-input-container {
-	box-shadow: inset var(--shadow-sm);
-}
-
 .monaco-workbench .interactive-session .interactive-input-part .chat-editor-container .interactive-input-editor .monaco-editor,
 .monaco-workbench .interactive-session .chat-editing-session .chat-editing-session-container {
 	border-radius: var(--radius-lg) var(--radius-lg) 0 0;
@@ -466,11 +461,7 @@
 }
 
 /* Input Boxes */
-.monaco-workbench .monaco-inputbox,
-.monaco-workbench .suggest-input-container {
-	box-shadow: inset var(--shadow-sm);
-	border: none;
-}
+
 
 .monaco-inputbox .monaco-action-bar .action-item .codicon,
 .monaco-workbench .search-container .input-box,
@@ -484,12 +475,6 @@
 	color: var(--vscode-icon-foreground) !important;
 }
 
-/* Buttons */
-
-.monaco-workbench .monaco-button:active {
-	box-shadow: var(--shadow-button-active);
-}
-
 /* Todo List Widget - remove shadows from buttons */
 .monaco-workbench.vs .chat-todo-list-widget .todo-list-expand .monaco-button,
 .monaco-workbench.vs .chat-todo-list-widget .todo-list-expand .monaco-button:hover,
@@ -628,7 +613,6 @@
 /* Notebook */
 
 .monaco-workbench .notebookOverlay .monaco-list-row .cell-editor-part:before {
-	box-shadow: inset var(--shadow-sm);
 	border-radius: var(--radius-md);
 }
 
@@ -653,7 +637,6 @@
 
 /* Command Center */
 .monaco-workbench .part.titlebar > .titlebar-container > .titlebar-center > .window-title > .command-center .action-item.command-center-center {
-	box-shadow: inset var(--shadow-sm) !important;
 	border-radius: var(--radius-lg) !important;
 	background: color-mix(in srgb, var(--vscode-commandCenter-background) 60%, transparent) !important;
 	-webkit-backdrop-filter: var(--backdrop-blur-md);
@@ -661,12 +644,10 @@
 }
 
 .monaco-workbench .part.titlebar > .titlebar-container > .titlebar-center > .window-title > .command-center .action-item.command-center-center:hover {
-	box-shadow: inset var(--shadow-sm) !important;
 	background: color-mix(in srgb, var(--vscode-commandCenter-activeBackground) 60%, transparent) !important;
 }
 
 .monaco-workbench .part.titlebar .command-center .agent-status-pill {
-	box-shadow: inset var(--shadow-sm);
 	border-color: var(--vscode-input-border);
 }
 
diff --git a/package-lock.json b/package-lock.json
index bb626ac34e2b9..b10be95329b35 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -103,7 +103,7 @@
         "css-loader": "^6.9.1",
         "debounce": "^1.0.0",
         "deemon": "^1.13.6",
-        "electron": "39.6.1",
+        "electron": "39.6.0",
         "eslint": "^9.36.0",
         "eslint-formatter-compact": "^8.40.0",
         "eslint-plugin-header": "3.1.1",
@@ -6826,9 +6826,9 @@
       "dev": true
     },
     "node_modules/electron": {
-      "version": "39.6.1",
-      "resolved": "https://registry.npmjs.org/electron/-/electron-39.6.1.tgz",
-      "integrity": "sha512-pgmTbWnT3rP+eo3EolO5EdNw5f7/x/0S7vP+eXC8Zyp2sWGjP4+kmo1RyeAYCChwIRWJFKQ2rQVl/ZkqwK6O2Q==",
+      "version": "39.6.0",
+      "resolved": "https://registry.npmjs.org/electron/-/electron-39.6.0.tgz",
+      "integrity": "sha512-KQK3sJ6JCyymY3HQxV0N/bVBQwKQETRW0N/+OYcrL9H6tZhpmTSaZY3qSxcruWrPIuouvoiP3Vk/JKUpw05ZIw==",
       "dev": true,
       "hasInstallScript": true,
       "license": "MIT",
diff --git a/package.json b/package.json
index 67e53ae161026..92aade626d160 100644
--- a/package.json
+++ b/package.json
@@ -1,7 +1,7 @@
 {
   "name": "code-oss-dev",
   "version": "1.110.0",
-  "distro": "3ddf7ca3e6b5b372de64cc436eb175522d30f8ab",
+  "distro": "8445dd0629deae101785f6b8e406ab3784a42fa6",
   "author": {
     "name": "Microsoft Corporation"
   },
@@ -172,7 +172,7 @@
     "css-loader": "^6.9.1",
     "debounce": "^1.0.0",
     "deemon": "^1.13.6",
-    "electron": "39.6.1",
+    "electron": "39.6.0",
     "eslint": "^9.36.0",
     "eslint-formatter-compact": "^8.40.0",
     "eslint-plugin-header": "3.1.1",
diff --git a/src/vs/editor/browser/viewParts/viewLines/viewLine.ts b/src/vs/editor/browser/viewParts/viewLines/viewLine.ts
index 4aaa9200561a9..3bf79d8b67925 100644
--- a/src/vs/editor/browser/viewParts/viewLines/viewLine.ts
+++ b/src/vs/editor/browser/viewParts/viewLines/viewLine.ts
@@ -116,7 +116,7 @@ export class ViewLine implements IVisibleLine {
 		const lineData = viewportData.getViewLineRenderingData(lineNumber);
 		const options = this._options;
 		const actualInlineDecorations = LineDecoration.filter(lineData.inlineDecorations, lineNumber, lineData.minColumn, lineData.maxColumn);
-		const renderWhitespace = (lineData.hasVariableFonts || options.experimentalWhitespaceRendering === 'off') ? options.renderWhitespace : 'none';
+		const renderWhitespace = options.experimentalWhitespaceRendering === 'off' ? options.renderWhitespace : 'none';
 		const allowFastRendering = !lineData.hasVariableFonts;
 
 		// Only send selection information when needed for rendering whitespace
diff --git a/src/vs/editor/browser/viewParts/whitespace/whitespace.ts b/src/vs/editor/browser/viewParts/whitespace/whitespace.ts
index 546d268130c31..42ee0e30dade4 100644
--- a/src/vs/editor/browser/viewParts/whitespace/whitespace.ts
+++ b/src/vs/editor/browser/viewParts/whitespace/whitespace.ts
@@ -122,9 +122,6 @@ export class WhitespaceOverlay extends DynamicViewOverlay {
 	}
 
 	private _applyRenderWhitespace(ctx: RenderingContext, lineNumber: number, selections: OffsetRange[] | null, lineData: ViewLineRenderingData): string {
-		if (lineData.hasVariableFonts) {
-			return '';
-		}
 		if (this._options.renderWhitespace === 'selection' && !selections) {
 			return '';
 		}
diff --git a/src/vs/sessions/browser/parts/chatBarPart.ts b/src/vs/sessions/browser/parts/chatBarPart.ts
index 9a74bb7021bd0..ebafc12e5c3b5 100644
--- a/src/vs/sessions/browser/parts/chatBarPart.ts
+++ b/src/vs/sessions/browser/parts/chatBarPart.ts
@@ -34,8 +34,7 @@ export class ChatBarPart extends AbstractPaneCompositePart {
 	static readonly placeholderViewContainersKey = 'workbench.chatbar.placeholderPanels';
 	static readonly viewContainersWorkspaceStateKey = 'workbench.chatbar.viewContainersWorkspaceState';
 
-	// Use the side bar dimensions
-	override readonly minimumWidth: number = 170;
+	override readonly minimumWidth: number = 300;
 	override readonly maximumWidth: number = Number.POSITIVE_INFINITY;
 	override readonly minimumHeight: number = 0;
 	override readonly maximumHeight: number = Number.POSITIVE_INFINITY;
@@ -44,21 +43,6 @@ export class ChatBarPart extends AbstractPaneCompositePart {
 		return this.layoutService.mainContainerDimension.height * 0.4;
 	}
 
-	get preferredWidth(): number | undefined {
-		const activeComposite = this.getActivePaneComposite();
-
-		if (!activeComposite) {
-			return undefined;
-		}
-
-		const width = activeComposite.getOptimalWidth();
-		if (typeof width !== 'number') {
-			return undefined;
-		}
-
-		return Math.max(width, 300);
-	}
-
 	readonly priority = LayoutPriority.High;
 
 	constructor(
diff --git a/src/vs/sessions/contrib/gitSync/browser/gitSync.contribution.ts b/src/vs/sessions/contrib/gitSync/browser/gitSync.contribution.ts
index 45e2dcf0af3b3..57f7e8a23ccbe 100644
--- a/src/vs/sessions/contrib/gitSync/browser/gitSync.contribution.ts
+++ b/src/vs/sessions/contrib/gitSync/browser/gitSync.contribution.ts
@@ -48,13 +48,17 @@ class GitSyncContribution extends Disposable implements IWorkbenchContribution {
 				return;
 			}
 
+			const repoDisposables = this._gitRepoDisposables.add(new DisposableStore());
 			this.gitService.openRepository(worktreeUri).then(repository => {
+				if (repoDisposables.isDisposed) {
+					return;
+				}
 				if (!repository) {
 					this._syncActionDisposable.clear();
 					contextKey.set(false);
 					return;
 				}
-				this._gitRepoDisposables.add(autorun(innerReader => {
+				repoDisposables.add(autorun(innerReader => {
 					const state = repository.state.read(innerReader);
 					const head = state.HEAD;
 					if (!head?.upstream) {
@@ -66,7 +70,7 @@ class GitSyncContribution extends Disposable implements IWorkbenchContribution {
 					const behind = head.behind ?? 0;
 					const hasSyncChanges = ahead > 0 || behind > 0;
 					contextKey.set(hasSyncChanges);
-					this._syncActionDisposable.value = registerSyncAction(ahead, behind);
+					this._syncActionDisposable.value = registerSyncAction(behind, ahead);
 				}));
 			});
 		}));
diff --git a/src/vs/sessions/contrib/workspace/browser/workspaceFolderManagement.ts b/src/vs/sessions/contrib/workspace/browser/workspaceFolderManagement.ts
index 44fa452df3abe..020c7861d46bf 100644
--- a/src/vs/sessions/contrib/workspace/browser/workspaceFolderManagement.ts
+++ b/src/vs/sessions/contrib/workspace/browser/workspaceFolderManagement.ts
@@ -13,6 +13,7 @@ import { IWorkspaceTrustManagementService } from '../../../../platform/workspace
 import { IUriIdentityService } from '../../../../platform/uriIdentity/common/uriIdentity.js';
 import { URI } from '../../../../base/common/uri.js';
 import { autorun } from '../../../../base/common/observable.js';
+import { IWorkspaceFolderCreationData } from '../../../../platform/workspaces/common/workspaces.js';
 
 export class WorkspaceFolderManagementContribution extends Disposable implements IWorkbenchContribution {
 
@@ -34,10 +35,10 @@ export class WorkspaceFolderManagementContribution extends Disposable implements
 
 	private async updateWorkspaceFoldersForSession(session: IActiveSessionItem | undefined): Promise<void> {
 		await this.manageTrustWorkspaceForSession(session);
-		const activeSessionRepo = session?.providerType === AgentSessionProviders.Background ? session.worktree ?? session.repository : undefined;
+		const activeSessionFolderData = this.getActiveSessionFolderData(session);
 		const currentRepo = this.workspaceContextService.getWorkspace().folders[0]?.uri;
 
-		if (!activeSessionRepo) {
+		if (!activeSessionFolderData) {
 			if (currentRepo) {
 				await this.workspaceEditingService.removeFolders([currentRepo], true);
 			}
@@ -45,15 +46,34 @@ export class WorkspaceFolderManagementContribution extends Disposable implements
 		}
 
 		if (!currentRepo) {
-			await this.workspaceEditingService.addFolders([{ uri: activeSessionRepo }], true);
+			await this.workspaceEditingService.addFolders([activeSessionFolderData], true);
 			return;
 		}
 
-		if (this.uriIdentityService.extUri.isEqual(currentRepo, activeSessionRepo)) {
+		if (this.uriIdentityService.extUri.isEqual(currentRepo, activeSessionFolderData.uri)) {
 			return;
 		}
 
-		await this.workspaceEditingService.updateFolders(0, 1, [{ uri: activeSessionRepo }], true);
+		await this.workspaceEditingService.updateFolders(0, 1, [activeSessionFolderData], true);
+	}
+
+	private getActiveSessionFolderData(session: IActiveSessionItem | undefined): IWorkspaceFolderCreationData | undefined {
+		if (session?.providerType !== AgentSessionProviders.Background) {
+			return undefined;
+		}
+
+		if (session.worktree) {
+			return {
+				uri: session.worktree,
+				name: session.repository ? `${this.uriIdentityService.extUri.basename(session.repository)} (worktree)` : undefined
+			};
+		}
+
+		if (session.repository) {
+			return { uri: session.repository };
+		}
+
+		return undefined;
 	}
 
 	private async manageTrustWorkspaceForSession(session: IActiveSessionItem | undefined): Promise<void> {
diff --git a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingActions.ts b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingActions.ts
index 460a79c2b5716..2e6371ba03160 100644
--- a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingActions.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingActions.ts
@@ -38,6 +38,7 @@ import { CHAT_CATEGORY } from '../actions/chatActions.js';
 import { ChatTreeItem, IChatWidget, IChatWidgetService } from '../chat.js';
 import { IAgentSession, isAgentSession } from '../agentSessions/agentSessionsModel.js';
 import { AgentSessionProviders } from '../agentSessions/agentSessions.js';
+import { IsSessionsWindowContext } from '../../../../common/contextkeys.js';
 
 export abstract class EditingSessionAction extends Action2 {
 
@@ -362,7 +363,7 @@ export class ViewAllSessionChangesAction extends Action2 {
 					id: MenuId.AgentSessionItemToolbar,
 					group: 'navigation',
 					order: 0,
-					when: ChatContextKeys.hasAgentSessionChanges
+					when: ContextKeyExpr.and(ChatContextKeys.hasAgentSessionChanges, IsSessionsWindowContext.negate())
 				}
 			],
 		});
diff --git a/src/vs/workbench/contrib/chat/browser/chatTipCatalog.ts b/src/vs/workbench/contrib/chat/browser/chatTipCatalog.ts
new file mode 100644
index 0000000000000..d130efd72758d
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/chatTipCatalog.ts
@@ -0,0 +1,363 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { MarkdownString } from '../../../../base/common/htmlContent.js';
+import { localize } from '../../../../nls.js';
+import { ContextKeyExpr, ContextKeyExpression } from '../../../../platform/contextkey/common/contextkey.js';
+import { IKeybindingService } from '../../../../platform/keybinding/common/keybinding.js';
+import { MenuRegistry } from '../../../../platform/actions/common/actions.js';
+import { ChatContextKeys } from '../common/actions/chatContextKeys.js';
+import { ChatConfiguration, ChatModeKind } from '../common/constants.js';
+import { localChatSessionType } from '../common/chatSessionsService.js';
+import { ITipExclusionConfig } from './chatTipEligibilityTracker.js';
+import { TipTrackingCommands } from './chatTipStorageKeys.js';
+import {
+	GENERATE_AGENT_COMMAND_ID,
+	GENERATE_ON_DEMAND_INSTRUCTIONS_COMMAND_ID,
+	GENERATE_PROMPT_COMMAND_ID,
+	GENERATE_SKILL_COMMAND_ID,
+} from './actions/chatActions.js';
+
+/**
+ * Context provided to tip builders for dynamic message construction.
+ */
+export interface ITipBuildContext {
+	/**
+	 * Keybinding service for looking up keyboard shortcuts.
+	 */
+	readonly keybindingService: IKeybindingService;
+}
+
+/**
+ * Gets the display label for a command, looking it up from MenuRegistry.
+ * Falls back to extracting a readable name from the command ID.
+ */
+export function getCommandLabel(commandId: string): string {
+	const command = MenuRegistry.getCommand(commandId);
+	if (command?.title) {
+		// Handle both string and ILocalizedString formats
+		return typeof command.title === 'string' ? command.title : command.title.value;
+	}
+	// Fallback: extract readable name from command ID
+	// e.g., 'workbench.action.chat.openEditSession' -> 'openEditSession'
+	const parts = commandId.split('.');
+	return parts[parts.length - 1];
+}
+
+/**
+ * Formats a keybinding for display in a tip message.
+ * Returns empty string if no keybinding is bound.
+ */
+function formatKeybinding(ctx: ITipBuildContext, commandId: string): string {
+	const kb = ctx.keybindingService.lookupKeybinding(commandId);
+	return kb ? ` (${kb.getLabel()})` : '';
+}
+
+/**
+ * Extracts command IDs from command: links in a markdown string.
+ * Used to automatically populate enabledCommands for trusted markdown.
+ */
+export function extractCommandIds(markdown: string): string[] {
+	const commandPattern = /\[.*?\]\(command:([^?\s)]+)/g;
+	const commands = new Set<string>();
+	let match;
+	while ((match = commandPattern.exec(markdown)) !== null) {
+		commands.add(match[1]);
+	}
+	return [...commands];
+}
+
+/**
+ * Interface for tip definitions in the catalog.
+ */
+export interface ITipDefinition extends ITipExclusionConfig {
+	readonly id: string;
+	/**
+	 * Builds the tip message dynamically at runtime.
+	 * This enables keybindings and command labels to be looked up fresh.
+	 * The returned MarkdownString should NOT include the "Tip:" prefix.
+	 */
+	buildMessage(ctx: ITipBuildContext): MarkdownString;
+	/**
+	 * When clause expression that determines if this tip is eligible to be shown.
+	 */
+	readonly when?: ContextKeyExpression;
+	/**
+	 * Chat model IDs for which this tip is eligible (lowercase).
+	 */
+	readonly onlyWhenModelIds?: readonly string[];
+	/**
+	 * Setting keys that, if changed from default, make this tip ineligible.
+	 */
+	readonly excludeWhenSettingsChanged?: readonly string[];
+	/**
+	 * Command IDs that dismiss this tip when clicked from the tip markdown.
+	 */
+	readonly dismissWhenCommandsClicked?: readonly string[];
+}
+
+// -----------------------------------------------------------------------------
+// Tip Catalog
+// -----------------------------------------------------------------------------
+
+/**
+ * Static catalog of tips. Tips are built dynamically at runtime to enable
+ * keybindings and command labels to be resolved fresh.
+ */
+export const TIP_CATALOG: readonly ITipDefinition[] = [
+	{
+		id: 'tip.switchToAuto',
+		buildMessage(ctx) {
+			const label = getCommandLabel('workbench.action.chat.openModelPicker');
+			const kb = formatKeybinding(ctx, 'workbench.action.chat.openModelPicker');
+			return new MarkdownString(
+				localize(
+					'tip.switchToAuto',
+					"Using gpt-4.1? Try switching to [{0}](command:workbench.action.chat.openModelPicker){1} for better coding performance.",
+					label,
+					kb
+				)
+			);
+		},
+		onlyWhenModelIds: ['gpt-4.1'],
+	},
+	{
+		id: 'tip.createInstruction',
+		buildMessage(ctx) {
+			const kb = formatKeybinding(ctx, GENERATE_ON_DEMAND_INSTRUCTIONS_COMMAND_ID);
+			return new MarkdownString(
+				localize(
+					'tip.createInstruction',
+					"Use [{0}](command:{1}){2} to generate an on-demand instructions file with the agent.",
+					'/create-instructions',
+					GENERATE_ON_DEMAND_INSTRUCTIONS_COMMAND_ID,
+					kb
+				)
+			);
+		},
+		when: ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
+		excludeWhenCommandsExecuted: [
+			GENERATE_ON_DEMAND_INSTRUCTIONS_COMMAND_ID,
+			TipTrackingCommands.CreateAgentInstructionsUsed,
+		],
+	},
+	{
+		id: 'tip.createPrompt',
+		buildMessage(ctx) {
+			const kb = formatKeybinding(ctx, GENERATE_PROMPT_COMMAND_ID);
+			return new MarkdownString(
+				localize(
+					'tip.createPrompt',
+					"Use [{0}](command:{1}){2} to generate a reusable prompt file with the agent.",
+					'/create-prompt',
+					GENERATE_PROMPT_COMMAND_ID,
+					kb
+				)
+			);
+		},
+		when: ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
+		excludeWhenCommandsExecuted: [
+			GENERATE_PROMPT_COMMAND_ID,
+			TipTrackingCommands.CreatePromptUsed,
+		],
+	},
+	{
+		id: 'tip.createAgent',
+		buildMessage(ctx) {
+			const kb = formatKeybinding(ctx, GENERATE_AGENT_COMMAND_ID);
+			return new MarkdownString(
+				localize(
+					'tip.createAgent',
+					"Use [{0}](command:{1}){2} to scaffold a custom agent for your workflow.",
+					'/create-agent',
+					GENERATE_AGENT_COMMAND_ID,
+					kb
+				)
+			);
+		},
+		when: ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
+		excludeWhenCommandsExecuted: [
+			GENERATE_AGENT_COMMAND_ID,
+			TipTrackingCommands.CreateAgentUsed,
+		],
+	},
+	{
+		id: 'tip.createSkill',
+		buildMessage(ctx) {
+			const kb = formatKeybinding(ctx, GENERATE_SKILL_COMMAND_ID);
+			return new MarkdownString(
+				localize(
+					'tip.createSkill',
+					"Use [{0}](command:{1}){2} to create a skill the agent can load when relevant.",
+					'/create-skill',
+					GENERATE_SKILL_COMMAND_ID,
+					kb
+				)
+			);
+		},
+		when: ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
+		excludeWhenCommandsExecuted: [
+			GENERATE_SKILL_COMMAND_ID,
+			TipTrackingCommands.CreateSkillUsed,
+		],
+	},
+	{
+		id: 'tip.agentMode',
+		buildMessage(ctx) {
+			const label = getCommandLabel('workbench.action.chat.openEditSession');
+			const kb = formatKeybinding(ctx, 'workbench.action.chat.openEditSession');
+			return new MarkdownString(
+				localize(
+					'tip.agentMode',
+					"Try [{0}](command:workbench.action.chat.openEditSession){1} to make edits across your project and run commands.",
+					label,
+					kb
+				)
+			);
+		},
+		when: ChatContextKeys.chatModeKind.notEqualsTo(ChatModeKind.Agent),
+		excludeWhenModesUsed: [ChatModeKind.Agent],
+	},
+	{
+		id: 'tip.planMode',
+		buildMessage(ctx) {
+			const kb = formatKeybinding(ctx, 'workbench.action.chat.openPlan');
+			return new MarkdownString(
+				localize(
+					'tip.planMode',
+					"Try the [{0}](command:workbench.action.chat.openPlan){1} to research and plan before implementing changes.",
+					'Plan agent',
+					kb
+				)
+			);
+		},
+		when: ChatContextKeys.chatModeName.notEqualsTo('Plan'),
+		excludeWhenCommandsExecuted: ['workbench.action.chat.openPlan'],
+		excludeWhenModesUsed: ['Plan'],
+	},
+	{
+		id: 'tip.attachFiles',
+		buildMessage() {
+			return new MarkdownString(
+				localize('tip.attachFiles', "Reference files or folders with # to give the agent more context about the task.")
+			);
+		},
+		excludeWhenCommandsExecuted: [
+			'workbench.action.chat.attachContext',
+			'workbench.action.chat.attachFile',
+			'workbench.action.chat.attachFolder',
+			'workbench.action.chat.attachSelection',
+			TipTrackingCommands.AttachFilesReferenceUsed,
+		],
+	},
+	{
+		id: 'tip.codeActions',
+		buildMessage() {
+			return new MarkdownString(
+				localize('tip.codeActions', "Select a code block in the editor and right-click to access more AI actions.")
+			);
+		},
+		excludeWhenCommandsExecuted: ['inlineChat.start'],
+	},
+	{
+		id: 'tip.undoChanges',
+		buildMessage() {
+			return new MarkdownString(
+				localize('tip.undoChanges', "Select \"Restore Checkpoint\" to undo changes after that point in the chat conversation.")
+			);
+		},
+		when: ContextKeyExpr.and(
+			ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
+			ContextKeyExpr.or(
+				ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
+				ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Edit),
+			),
+		),
+		excludeWhenCommandsExecuted: ['workbench.action.chat.restoreCheckpoint', 'workbench.action.chat.restoreLastCheckpoint'],
+	},
+	{
+		id: 'tip.messageQueueing',
+		buildMessage() {
+			return new MarkdownString(
+				localize('tip.messageQueueing', "Steer the agent mid-task by sending follow-up messages. They queue and apply in order.")
+			);
+		},
+		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
+		excludeWhenCommandsExecuted: ['workbench.action.chat.queueMessage', 'workbench.action.chat.steerWithMessage'],
+	},
+	{
+		id: 'tip.yoloMode',
+		buildMessage() {
+			return new MarkdownString(
+				localize(
+					'tip.yoloMode',
+					"Enable [{0}](command:workbench.action.openSettings?%5B%22{1}%22%5D) to give the agent full control without manual confirmation.",
+					'auto approve',
+					ChatConfiguration.GlobalAutoApprove
+				)
+			);
+		},
+		when: ContextKeyExpr.and(
+			ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
+			ContextKeyExpr.notEquals('config.chat.tools.global.autoApprove', true),
+		),
+		excludeWhenSettingsChanged: [ChatConfiguration.GlobalAutoApprove],
+		dismissWhenCommandsClicked: ['workbench.action.openSettings'],
+	},
+	{
+		id: 'tip.agenticBrowser',
+		buildMessage() {
+			return new MarkdownString(
+				localize(
+					'tip.agenticBrowser',
+					"Enable [{0}](command:workbench.action.openSettings?%5B%22workbench.browser.enableChatTools%22%5D) to let the agent open and interact with pages in the Integrated Browser.",
+					'agentic browser integration'
+				)
+			);
+		},
+		when: ContextKeyExpr.and(
+			ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
+			ContextKeyExpr.notEquals('config.workbench.browser.enableChatTools', true),
+		),
+		excludeWhenSettingsChanged: ['workbench.browser.enableChatTools'],
+		dismissWhenCommandsClicked: ['workbench.action.openSettings'],
+	},
+	{
+		id: 'tip.mermaid',
+		buildMessage() {
+			return new MarkdownString(
+				localize('tip.mermaid', "Ask the agent to draw an architectural diagram or flow chart; it can render Mermaid diagrams directly in chat.")
+			);
+		},
+		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
+		excludeWhenToolsInvoked: ['renderMermaidDiagram'],
+	},
+	{
+		id: 'tip.subagents',
+		buildMessage() {
+			return new MarkdownString(
+				localize('tip.subagents', "Ask the agent to work in parallel to complete large tasks faster.")
+			);
+		},
+		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
+		excludeWhenToolsInvoked: ['runSubagent'],
+	},
+	{
+		id: 'tip.thinkingPhrases',
+		buildMessage() {
+			return new MarkdownString(
+				localize(
+					'tip.thinkingPhrases',
+					"Customize the loading messages shown while the agent works with [{0}](command:workbench.action.openSettings?%5B%22{1}%22%5D).",
+					'thinking phrases',
+					ChatConfiguration.ThinkingPhrases
+				)
+			);
+		},
+		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
+		excludeWhenSettingsChanged: [ChatConfiguration.ThinkingPhrases],
+		dismissWhenCommandsClicked: ['workbench.action.openSettings'],
+	},
+];
diff --git a/src/vs/workbench/contrib/chat/browser/chatTipEligibilityTracker.ts b/src/vs/workbench/contrib/chat/browser/chatTipEligibilityTracker.ts
new file mode 100644
index 0000000000000..df72fa41ab419
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/chatTipEligibilityTracker.ts
@@ -0,0 +1,327 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { CancellationToken } from '../../../../base/common/cancellation.js';
+import { Disposable, MutableDisposable } from '../../../../base/common/lifecycle.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
+import { ChatContextKeys } from '../common/actions/chatContextKeys.js';
+import { AgentFileType, IPromptsService } from '../common/promptSyntax/service/promptsService.js';
+import { PromptsType } from '../common/promptSyntax/promptTypes.js';
+import { ILanguageModelToolsService } from '../common/tools/languageModelToolsService.js';
+import { TipEligibilityStorageKeys } from './chatTipStorageKeys.js';
+
+/**
+ * Interface for tip definitions that have exclusion criteria tracked by this class.
+ * This subset is all TipEligibilityTracker needs to know about tip definitions.
+ */
+export interface ITipExclusionConfig {
+	readonly id: string;
+	/** Command IDs that, if ever executed, make this tip ineligible. */
+	readonly excludeWhenCommandsExecuted?: readonly string[];
+	/** Chat mode names that, if ever used, make this tip ineligible. */
+	readonly excludeWhenModesUsed?: readonly string[];
+	/** Tool IDs that, if ever invoked, make this tip ineligible. */
+	readonly excludeWhenToolsInvoked?: readonly string[];
+	/** File-based exclusion configuration. */
+	readonly excludeWhenPromptFilesExist?: {
+		readonly promptType: PromptsType;
+		readonly agentFileType?: AgentFileType;
+		readonly excludeUntilChecked?: boolean;
+	};
+}
+
+/**
+ * Tracks user-level signals that determine whether certain tips should be
+ * excluded. Persists state to application storage and disposes listeners once all
+ * signals of interest have been observed.
+ */
+export class TipEligibilityTracker extends Disposable {
+
+	private readonly _executedCommands: Set<string>;
+	private readonly _usedModes: Set<string>;
+	private readonly _invokedTools: Set<string>;
+
+	private readonly _pendingCommands: Set<string>;
+	private readonly _pendingModes: Set<string>;
+	private readonly _pendingTools: Set<string>;
+
+	private readonly _commandListener = this._register(new MutableDisposable());
+	private readonly _toolListener = this._register(new MutableDisposable());
+
+	/**
+	 * Tip IDs excluded because prompt files of the required type exist in the workspace.
+	 * Tips with `excludeUntilChecked` are pre-added and removed if no files are found.
+	 */
+	private readonly _excludedByFiles = new Set<string>();
+
+	/** Tips that have file-based exclusions, kept for re-checks. */
+	private readonly _tipsWithFileExclusions: readonly ITipExclusionConfig[];
+
+	/** Generation counter per tip ID to discard stale async file-check results. */
+	private readonly _fileCheckGeneration = new Map<string, number>();
+	private readonly _fileChecksInFlight = new Map<string, Promise<void>>();
+
+	constructor(
+		tips: readonly ITipExclusionConfig[],
+		@ICommandService commandService: ICommandService,
+		@IStorageService private readonly _storageService: IStorageService,
+		@IPromptsService private readonly _promptsService: IPromptsService,
+		@ILanguageModelToolsService private readonly _languageModelToolsService: ILanguageModelToolsService,
+		@ILogService private readonly _logService: ILogService,
+	) {
+		super();
+
+		// --- Restore persisted state -------------------------------------------
+
+		const storedCmds = this._readApplicationWithProfileFallback(TipEligibilityStorageKeys.ExecutedCommands);
+		this._executedCommands = new Set<string>(storedCmds ? JSON.parse(storedCmds) : []);
+
+		const storedModes = this._readApplicationWithProfileFallback(TipEligibilityStorageKeys.UsedModes);
+		this._usedModes = new Set<string>(storedModes ? JSON.parse(storedModes) : []);
+
+		const storedTools = this._readApplicationWithProfileFallback(TipEligibilityStorageKeys.InvokedTools);
+		this._invokedTools = new Set<string>(storedTools ? JSON.parse(storedTools) : []);
+
+		// --- Derive what still needs tracking ----------------------------------
+
+		this._pendingCommands = new Set<string>();
+		for (const tip of tips) {
+			for (const cmd of tip.excludeWhenCommandsExecuted ?? []) {
+				if (!this._executedCommands.has(cmd)) {
+					this._pendingCommands.add(cmd);
+				}
+			}
+		}
+
+		this._pendingModes = new Set<string>();
+		for (const tip of tips) {
+			for (const mode of tip.excludeWhenModesUsed ?? []) {
+				if (!this._usedModes.has(mode)) {
+					this._pendingModes.add(mode);
+				}
+			}
+		}
+
+		this._pendingTools = new Set<string>();
+		for (const tip of tips) {
+			for (const toolId of tip.excludeWhenToolsInvoked ?? []) {
+				if (!this._invokedTools.has(toolId)) {
+					this._pendingTools.add(toolId);
+				}
+			}
+		}
+
+		// --- Set up command listener (auto-disposes when all seen) --------------
+
+		if (this._pendingCommands.size > 0) {
+			this._commandListener.value = commandService.onDidExecuteCommand(e => {
+				this.recordCommandExecuted(e.commandId);
+			});
+		}
+
+		// --- Set up tool listener (auto-disposes when all seen) -----------------
+
+		if (this._pendingTools.size > 0) {
+			this._toolListener.value = this._languageModelToolsService.onDidInvokeTool(e => {
+				// Track explicit tool IDs
+				if (this._pendingTools.has(e.toolId)) {
+					this._invokedTools.add(e.toolId);
+					this._pendingTools.delete(e.toolId);
+
+					this._persistSet(TipEligibilityStorageKeys.InvokedTools, this._invokedTools);
+				}
+
+				if (this._pendingTools.size === 0) {
+					this._toolListener.clear();
+				}
+			});
+		}
+
+		// --- Async file checks -------------------------------------------------
+
+		this._tipsWithFileExclusions = tips.filter(t => t.excludeWhenPromptFilesExist);
+		for (const tip of this._tipsWithFileExclusions) {
+			if (tip.excludeWhenPromptFilesExist!.excludeUntilChecked) {
+				this._excludedByFiles.add(tip.id);
+			}
+			this._checkForPromptFiles(tip);
+		}
+
+		// Re-check agent file exclusions when custom agents change (covers late discovery)
+		this._register(this._promptsService.onDidChangeCustomAgents(() => {
+			for (const tip of this._tipsWithFileExclusions) {
+				if (tip.excludeWhenPromptFilesExist!.promptType === PromptsType.agent) {
+					this._checkForPromptFiles(tip);
+				}
+			}
+		}));
+	}
+
+	recordCommandExecuted(commandId: string): void {
+		if (!this._pendingCommands.has(commandId)) {
+			return;
+		}
+
+		this._executedCommands.add(commandId);
+		this._persistSet(TipEligibilityStorageKeys.ExecutedCommands, this._executedCommands);
+		this._pendingCommands.delete(commandId);
+
+		if (this._pendingCommands.size === 0) {
+			this._commandListener.clear();
+		}
+	}
+
+	/**
+	 * Records the current chat mode (kind + name) so future tip eligibility
+	 * checks can exclude mode-related tips. No-ops once all tracked modes
+	 * have been observed.
+	 */
+	recordCurrentMode(contextKeyService: IContextKeyService): void {
+		if (this._pendingModes.size === 0) {
+			return;
+		}
+
+		let changed = false;
+		const kind = contextKeyService.getContextKeyValue<string>(ChatContextKeys.chatModeKind.key);
+		if (kind && !this._usedModes.has(kind)) {
+			this._usedModes.add(kind);
+			this._pendingModes.delete(kind);
+			changed = true;
+		}
+		const name = contextKeyService.getContextKeyValue<string>(ChatContextKeys.chatModeName.key);
+		if (name && !this._usedModes.has(name)) {
+			this._usedModes.add(name);
+			this._pendingModes.delete(name);
+			changed = true;
+		}
+		if (changed) {
+			this._persistSet(TipEligibilityStorageKeys.UsedModes, this._usedModes);
+		}
+	}
+
+	/**
+	 * Returns `true` when the tip should be **excluded** from the eligible set.
+	 */
+	isExcluded(tip: ITipExclusionConfig): boolean {
+		if (tip.excludeWhenCommandsExecuted) {
+			for (const cmd of tip.excludeWhenCommandsExecuted) {
+				if (this._executedCommands.has(cmd)) {
+					this._logService.debug('#ChatTips: tip excluded because command was executed', tip.id, cmd);
+					return true;
+				}
+			}
+		}
+		if (tip.excludeWhenModesUsed) {
+			for (const mode of tip.excludeWhenModesUsed) {
+				if (this._usedModes.has(mode)) {
+					this._logService.debug('#ChatTips: tip excluded because mode was used', tip.id, mode);
+					return true;
+				}
+			}
+		}
+		if (tip.excludeWhenToolsInvoked) {
+			for (const toolId of tip.excludeWhenToolsInvoked) {
+				if (this._invokedTools.has(toolId)) {
+					this._logService.debug('#ChatTips: tip excluded because tool was invoked', tip.id, toolId);
+					return true;
+				}
+			}
+		}
+		if (tip.excludeWhenPromptFilesExist && this._excludedByFiles.has(tip.id)) {
+			this._logService.debug('#ChatTips: tip excluded because prompt files exist', tip.id);
+			return true;
+		}
+		return false;
+	}
+
+	/**
+	 * Revalidates all file-based tip exclusions. Tips with `excludeUntilChecked`
+	 * are conservatively hidden until the re-check completes.
+	 */
+	refreshPromptFileExclusions(): void {
+		for (const tip of this._tipsWithFileExclusions) {
+			if (tip.excludeWhenPromptFilesExist!.excludeUntilChecked) {
+				this._excludedByFiles.add(tip.id);
+			}
+			this._checkForPromptFiles(tip);
+		}
+	}
+
+	private async _checkForPromptFiles(tip: ITipExclusionConfig): Promise<void> {
+		const inFlight = this._fileChecksInFlight.get(tip.id);
+		if (inFlight) {
+			await inFlight;
+			return;
+		}
+
+		const checkPromise = this._doCheckForPromptFiles(tip);
+		this._fileChecksInFlight.set(tip.id, checkPromise);
+		try {
+			await checkPromise;
+		} finally {
+			if (this._fileChecksInFlight.get(tip.id) === checkPromise) {
+				this._fileChecksInFlight.delete(tip.id);
+			}
+		}
+	}
+
+	private async _doCheckForPromptFiles(tip: ITipExclusionConfig): Promise<void> {
+		const config = tip.excludeWhenPromptFilesExist!;
+		const generation = (this._fileCheckGeneration.get(tip.id) ?? 0) + 1;
+		this._fileCheckGeneration.set(tip.id, generation);
+
+		try {
+			const [promptFiles, agentInstructions] = await Promise.all([
+				this._promptsService.listPromptFiles(config.promptType, CancellationToken.None),
+				config.agentFileType ? this._promptsService.listAgentInstructions(CancellationToken.None) : Promise.resolve([]),
+			]);
+
+			// Discard stale result if a newer check was started while we were awaiting
+			if (this._fileCheckGeneration.get(tip.id) !== generation) {
+				return;
+			}
+
+			const hasPromptFiles = promptFiles.length > 0;
+			const hasAgentFile = config.agentFileType
+				? agentInstructions.some(f => f.type === config.agentFileType)
+				: false;
+			const hasPromptFilesOrAgentFile = hasPromptFiles || hasAgentFile;
+
+			if (hasPromptFilesOrAgentFile) {
+				this._excludedByFiles.add(tip.id);
+			} else {
+				this._excludedByFiles.delete(tip.id);
+			}
+		} catch {
+			if (this._fileCheckGeneration.get(tip.id) !== generation) {
+				return;
+			}
+			if (config.excludeUntilChecked) {
+				this._excludedByFiles.add(tip.id);
+			}
+		}
+	}
+
+	private _persistSet(key: string, set: Set<string>): void {
+		this._storageService.store(key, JSON.stringify([...set]), StorageScope.APPLICATION, StorageTarget.MACHINE);
+	}
+
+	private _readApplicationWithProfileFallback(key: string): string | undefined {
+		const applicationValue = this._storageService.get(key, StorageScope.APPLICATION);
+		if (applicationValue) {
+			return applicationValue;
+		}
+
+		const profileValue = this._storageService.get(key, StorageScope.PROFILE);
+		if (profileValue) {
+			this._storageService.store(key, profileValue, StorageScope.APPLICATION, StorageTarget.MACHINE);
+		}
+
+		return profileValue;
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/chatTipService.ts b/src/vs/workbench/contrib/chat/browser/chatTipService.ts
index e4c5387b9c5a3..3bc000338552c 100644
--- a/src/vs/workbench/contrib/chat/browser/chatTipService.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatTipService.ts
@@ -5,28 +5,26 @@
 
 import { Emitter, Event } from '../../../../base/common/event.js';
 import { MarkdownString } from '../../../../base/common/htmlContent.js';
-import { ContextKeyExpr, ContextKeyExpression, IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
+import { IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
 import { createDecorator, IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
 import { IProductService } from '../../../../platform/product/common/productService.js';
 import { ChatContextKeys } from '../common/actions/chatContextKeys.js';
-import { ChatAgentLocation, ChatConfiguration, ChatModeKind } from '../common/constants.js';
+import { ChatAgentLocation, ChatConfiguration } from '../common/constants.js';
 import { ConfigurationTarget, IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { Disposable, MutableDisposable } from '../../../../base/common/lifecycle.js';
 import { ICommandService } from '../../../../platform/commands/common/commands.js';
 import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
-import { AgentFileType, IPromptsService } from '../common/promptSyntax/service/promptsService.js';
-import { PromptsType } from '../common/promptSyntax/promptTypes.js';
-import { CancellationToken } from '../../../../base/common/cancellation.js';
 import { localize } from '../../../../nls.js';
 import { ILogService } from '../../../../platform/log/common/log.js';
-import { ILanguageModelToolsService } from '../common/tools/languageModelToolsService.js';
-import { localChatSessionType } from '../common/chatSessionsService.js';
 import { IChatService } from '../common/chatService/chatService.js';
 import { CreateSlashCommandsUsageTracker } from './createSlashCommandsUsageTracker.js';
 import { ChatEntitlement, IChatEntitlementService } from '../../../services/chat/common/chatEntitlementService.js';
 import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
 import { ChatRequestDynamicVariablePart, ChatRequestSlashCommandPart, IParsedChatRequest } from '../common/requestParser/chatParserTypes.js';
-import { GENERATE_AGENT_COMMAND_ID, GENERATE_ON_DEMAND_INSTRUCTIONS_COMMAND_ID, GENERATE_PROMPT_COMMAND_ID, GENERATE_SKILL_COMMAND_ID } from './actions/chatActions.js';
+import { IKeybindingService } from '../../../../platform/keybinding/common/keybinding.js';
+import { TipEligibilityTracker } from './chatTipEligibilityTracker.js';
+import { extractCommandIds, ITipBuildContext, ITipDefinition, TIP_CATALOG } from './chatTipCatalog.js';
+import { ChatTipStorageKeys, TipTrackingCommands } from './chatTipStorageKeys.js';
 
 type ChatTipEvent = {
 	tipId: string;
@@ -42,11 +40,20 @@ type ChatTipClassification = {
 	comment: 'Tracks user interactions with chat tips to understand which tips resonate and which are dismissed.';
 };
 
-export const ATTACH_FILES_REFERENCE_TRACKING_COMMAND = 'chat.tips.attachFiles.referenceUsed';
-export const CREATE_AGENT_INSTRUCTIONS_TRACKING_COMMAND = 'chat.tips.createAgentInstructions.commandUsed';
-export const CREATE_PROMPT_TRACKING_COMMAND = 'chat.tips.createPrompt.commandUsed';
-export const CREATE_AGENT_TRACKING_COMMAND = 'chat.tips.createAgent.commandUsed';
-export const CREATE_SKILL_TRACKING_COMMAND = 'chat.tips.createSkill.commandUsed';
+// Re-export tracking commands for backwards compatibility
+export {
+	TipTrackingCommands,
+};
+/** @deprecated Use TipTrackingCommands.AttachFilesReferenceUsed */
+export const ATTACH_FILES_REFERENCE_TRACKING_COMMAND = TipTrackingCommands.AttachFilesReferenceUsed;
+/** @deprecated Use TipTrackingCommands.CreateAgentInstructionsUsed */
+export const CREATE_AGENT_INSTRUCTIONS_TRACKING_COMMAND = TipTrackingCommands.CreateAgentInstructionsUsed;
+/** @deprecated Use TipTrackingCommands.CreatePromptUsed */
+export const CREATE_PROMPT_TRACKING_COMMAND = TipTrackingCommands.CreatePromptUsed;
+/** @deprecated Use TipTrackingCommands.CreateAgentUsed */
+export const CREATE_AGENT_TRACKING_COMMAND = TipTrackingCommands.CreateAgentUsed;
+/** @deprecated Use TipTrackingCommands.CreateSkillUsed */
+export const CREATE_SKILL_TRACKING_COMMAND = TipTrackingCommands.CreateSkillUsed;
 
 export const IChatTipService = createDecorator<IChatTipService>('chatTipService');
 
@@ -118,6 +125,12 @@ export interface IChatTipService {
 	 */
 	navigateToPreviousTip(): IChatTip | undefined;
 
+	/**
+	 * Gets the next eligible tip after the current one, without requiring multiple tips.
+	 * Used after dismissing a tip to show the next available tip (even if it's the only one left).
+	 */
+	getNextEligibleTip(): IChatTip | undefined;
+
 	/**
 	 * Returns whether there are multiple eligible tips for navigation.
 	 */
@@ -129,508 +142,9 @@ export interface IChatTipService {
 	clearDismissedTips(): void;
 }
 
-export interface ITipDefinition {
-	readonly id: string;
-	readonly message: string;
-	/**
-	 * When clause expression that determines if this tip is eligible to be shown.
-	 * If undefined, the tip is always eligible.
-	 */
-	readonly when?: ContextKeyExpression;
-	/**
-	 * Command IDs that are allowed to be executed from this tip's markdown.
-	 */
-	readonly enabledCommands?: string[];
-	/**
-	 * Chat model IDs for which this tip is eligible.
-	 * Compared against the lowercased `chatModelId` context key.
-	 */
-	readonly onlyWhenModelIds?: readonly string[];
-	/**
-	 * Command IDs that, if ever executed in this workspace, make this tip ineligible.
-	 * The tip won't be shown if the user has already performed the action it suggests.
-	 */
-	readonly excludeWhenCommandsExecuted?: string[];
-	/**
-	 * Chat mode names that, if ever used in this workspace, make this tip ineligible.
-	 * The tip won't be shown if the user has already used the mode it suggests.
-	 * Matches against both mode kind (e.g. 'agent') and mode name (e.g. 'Plan').
-	 */
-	readonly excludeWhenModesUsed?: string[];
-	/**
-	 * Tool IDs that, if ever invoked in this workspace, make this tip ineligible.
-	 * The tip won't be shown if the tool it describes has already been used.
-	 */
-	readonly excludeWhenToolsInvoked?: string[];
-	/**
-	 * If set, exclude this tip when prompt files of the specified type exist in the workspace.
-	 */
-	readonly excludeWhenPromptFilesExist?: {
-		readonly promptType: PromptsType;
-		/** Also check for this specific agent instruction file type. */
-		readonly agentFileType?: AgentFileType;
-		/** If true, exclude the tip until the async file check completes. Default: false. */
-		readonly excludeUntilChecked?: boolean;
-	};
-	/**
-	 * Setting keys that, if changed from their default value, make this tip ineligible.
-	 * The tip won't be shown if the user has already customized the setting it describes.
-	 */
-	readonly excludeWhenSettingsChanged?: string[];
-	/**
-	 * Command IDs that dismiss this tip when clicked from the tip markdown
-	 * while the tip is currently shown.
-	 */
-	readonly dismissWhenCommandsClicked?: string[];
-}
-
-/**
- * Static catalog of tips. Each tip has an optional when clause for eligibility.
- */
-const TIP_CATALOG: ITipDefinition[] = [
-	{
-		id: 'tip.switchToAuto',
-		message: localize('tip.switchToAuto', "Tip: Using gpt-4.1? Try switching to [Auto](command:workbench.action.chat.openModelPicker) in the model picker for better coding performance."),
-		enabledCommands: ['workbench.action.chat.openModelPicker'],
-		onlyWhenModelIds: ['gpt-4.1'],
-	},
-	{
-		id: 'tip.createInstruction',
-		message: localize(
-			'tip.createInstruction',
-			"Tip: Use [/create-instructions](command:{0}) to generate an on-demand instructions file with the agent.",
-			GENERATE_ON_DEMAND_INSTRUCTIONS_COMMAND_ID
-		),
-		when: ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
-		enabledCommands: [GENERATE_ON_DEMAND_INSTRUCTIONS_COMMAND_ID],
-		excludeWhenCommandsExecuted: [
-			GENERATE_ON_DEMAND_INSTRUCTIONS_COMMAND_ID,
-			CREATE_AGENT_INSTRUCTIONS_TRACKING_COMMAND,
-		],
-	},
-	{
-		id: 'tip.createPrompt',
-		message: localize(
-			'tip.createPrompt',
-			"Tip: Use [/create-prompt](command:{0}) to generate a reusable prompt file with the agent.",
-			GENERATE_PROMPT_COMMAND_ID
-		),
-		when: ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
-		enabledCommands: [GENERATE_PROMPT_COMMAND_ID],
-		excludeWhenCommandsExecuted: [
-			GENERATE_PROMPT_COMMAND_ID,
-			CREATE_PROMPT_TRACKING_COMMAND,
-		],
-	},
-	{
-		id: 'tip.createAgent',
-		message: localize(
-			'tip.createAgent',
-			"Tip: Use [/create-agent](command:{0}) to scaffold a custom agent for your workflow.",
-			GENERATE_AGENT_COMMAND_ID
-		),
-		when: ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
-		enabledCommands: [GENERATE_AGENT_COMMAND_ID],
-		excludeWhenCommandsExecuted: [
-			GENERATE_AGENT_COMMAND_ID,
-			CREATE_AGENT_TRACKING_COMMAND,
-		],
-	},
-	{
-		id: 'tip.createSkill',
-		message: localize(
-			'tip.createSkill',
-			"Tip: Use [/create-skill](command:{0}) to create a skill the agent can load when relevant.",
-			GENERATE_SKILL_COMMAND_ID
-		),
-		when: ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
-		enabledCommands: [GENERATE_SKILL_COMMAND_ID],
-		excludeWhenCommandsExecuted: [
-			GENERATE_SKILL_COMMAND_ID,
-			CREATE_SKILL_TRACKING_COMMAND,
-		],
-	},
-	{
-		id: 'tip.agentMode',
-		message: localize('tip.agentMode', "Tip: Try [Agents](command:workbench.action.chat.openEditSession) to make edits across your project and run commands."),
-		when: ChatContextKeys.chatModeKind.notEqualsTo(ChatModeKind.Agent),
-		enabledCommands: ['workbench.action.chat.openEditSession'],
-		excludeWhenModesUsed: [ChatModeKind.Agent],
-	},
-	{
-		id: 'tip.planMode',
-		message: localize('tip.planMode', "Tip: Try the [Plan agent](command:workbench.action.chat.openPlan) to research and plan before implementing changes."),
-		when: ChatContextKeys.chatModeName.notEqualsTo('Plan'),
-		enabledCommands: ['workbench.action.chat.openPlan'],
-		excludeWhenCommandsExecuted: ['workbench.action.chat.openPlan'],
-		excludeWhenModesUsed: ['Plan'],
-	},
-	{
-		id: 'tip.attachFiles',
-		message: localize('tip.attachFiles', "Tip: Reference files or folders with # to give the agent more context about the task."),
-		excludeWhenCommandsExecuted: ['workbench.action.chat.attachContext', 'workbench.action.chat.attachFile', 'workbench.action.chat.attachFolder', 'workbench.action.chat.attachSelection', ATTACH_FILES_REFERENCE_TRACKING_COMMAND],
-	},
-	{
-		id: 'tip.codeActions',
-		message: localize('tip.codeActions', "Tip: Select a code block in the editor and right-click to access more AI actions."),
-		excludeWhenCommandsExecuted: ['inlineChat.start'],
-	},
-	{
-		id: 'tip.undoChanges',
-		message: localize('tip.undoChanges', "Tip: Select \"Restore Checkpoint\" to undo changes after that point in the chat conversation."),
-		when: ContextKeyExpr.and(
-			ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
-			ContextKeyExpr.or(
-				ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-				ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Edit),
-			),
-		),
-		excludeWhenCommandsExecuted: ['workbench.action.chat.restoreCheckpoint', 'workbench.action.chat.restoreLastCheckpoint'],
-	},
-	{
-		id: 'tip.messageQueueing',
-		message: localize('tip.messageQueueing', "Tip: Steer the agent mid-task by sending follow-up messages. They queue and apply in order."),
-		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-		excludeWhenCommandsExecuted: ['workbench.action.chat.queueMessage', 'workbench.action.chat.steerWithMessage'],
-	},
-	{
-		id: 'tip.yoloMode',
-		message: localize('tip.yoloMode', "Tip: Enable [auto approve](command:workbench.action.openSettings?%5B%22chat.tools.global.autoApprove%22%5D) to give the agent full control without manual confirmation."),
-		when: ContextKeyExpr.and(
-			ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-			ContextKeyExpr.notEquals('config.chat.tools.global.autoApprove', true),
-		),
-		enabledCommands: ['workbench.action.openSettings'],
-		excludeWhenSettingsChanged: [ChatConfiguration.GlobalAutoApprove],
-		dismissWhenCommandsClicked: ['workbench.action.openSettings'],
-	},
-	{
-		id: 'tip.agenticBrowser',
-		message: localize('tip.agenticBrowser', "Tip: Enable [agentic browser integration](command:workbench.action.openSettings?%5B%22workbench.browser.enableChatTools%22%5D) to let the agent open and interact with pages in the Integrated Browser."),
-		when: ContextKeyExpr.and(
-			ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-			ContextKeyExpr.notEquals('config.workbench.browser.enableChatTools', true),
-		),
-		enabledCommands: ['workbench.action.openSettings'],
-		excludeWhenSettingsChanged: ['workbench.browser.enableChatTools'],
-		dismissWhenCommandsClicked: ['workbench.action.openSettings'],
-	},
-	{
-		id: 'tip.mermaid',
-		message: localize('tip.mermaid', "Tip: Ask the agent to draw an architectural diagram or flow chart; it can render Mermaid diagrams directly in chat."),
-		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-		excludeWhenToolsInvoked: ['renderMermaidDiagram'],
-	},
-	{
-		id: 'tip.subagents',
-		message: localize('tip.subagents', "Tip: Ask the agent to work in parallel to complete large tasks faster."),
-		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-		excludeWhenToolsInvoked: ['runSubagent'],
-	},
-	{
-		id: 'tip.thinkingPhrases',
-		message: localize('tip.thinkingPhrases', "Tip: Customize the loading messages shown while the agent works with [thinking phrases](command:workbench.action.openSettings?%5B%22chat.agent.thinking.phrases%22%5D)."),
-		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-		enabledCommands: ['workbench.action.openSettings'],
-		excludeWhenSettingsChanged: ['chat.agent.thinking.phrases'],
-		dismissWhenCommandsClicked: ['workbench.action.openSettings'],
-	},
-];
-
-/**
- * Tracks user-level signals that determine whether certain tips should be
- * excluded. Persists state to application storage and disposes listeners once all
- * signals of interest have been observed.
- */
-export class TipEligibilityTracker extends Disposable {
-
-	private static readonly _COMMANDS_STORAGE_KEY = 'chat.tips.executedCommands';
-	private static readonly _MODES_STORAGE_KEY = 'chat.tips.usedModes';
-	private static readonly _TOOLS_STORAGE_KEY = 'chat.tips.invokedTools';
-
-	private readonly _executedCommands: Set<string>;
-	private readonly _usedModes: Set<string>;
-	private readonly _invokedTools: Set<string>;
-
-	private readonly _pendingCommands: Set<string>;
-	private readonly _pendingModes: Set<string>;
-	private readonly _pendingTools: Set<string>;
-
-	private readonly _commandListener = this._register(new MutableDisposable());
-	private readonly _toolListener = this._register(new MutableDisposable());
-
-	/**
-	 * Tip IDs excluded because prompt files of the required type exist in the workspace.
-	 * Tips with `excludeUntilChecked` are pre-added and removed if no files are found.
-	 */
-	private readonly _excludedByFiles = new Set<string>();
-
-	/** Tips that have file-based exclusions, kept for re-checks. */
-	private readonly _tipsWithFileExclusions: readonly ITipDefinition[];
-
-	/** Generation counter per tip ID to discard stale async file-check results. */
-	private readonly _fileCheckGeneration = new Map<string, number>();
-	private readonly _fileChecksInFlight = new Map<string, Promise<void>>();
-
-	constructor(
-		tips: readonly ITipDefinition[],
-		@ICommandService commandService: ICommandService,
-		@IStorageService private readonly _storageService: IStorageService,
-		@IPromptsService private readonly _promptsService: IPromptsService,
-		@ILanguageModelToolsService private readonly _languageModelToolsService: ILanguageModelToolsService,
-		@ILogService private readonly _logService: ILogService,
-	) {
-		super();
-
-		// --- Restore persisted state -------------------------------------------
-
-		const storedCmds = this._readApplicationWithProfileFallback(TipEligibilityTracker._COMMANDS_STORAGE_KEY);
-		this._executedCommands = new Set<string>(storedCmds ? JSON.parse(storedCmds) : []);
-
-		const storedModes = this._readApplicationWithProfileFallback(TipEligibilityTracker._MODES_STORAGE_KEY);
-		this._usedModes = new Set<string>(storedModes ? JSON.parse(storedModes) : []);
-
-		const storedTools = this._readApplicationWithProfileFallback(TipEligibilityTracker._TOOLS_STORAGE_KEY);
-		this._invokedTools = new Set<string>(storedTools ? JSON.parse(storedTools) : []);
-
-		// --- Derive what still needs tracking ----------------------------------
-
-		this._pendingCommands = new Set<string>();
-		for (const tip of tips) {
-			for (const cmd of tip.excludeWhenCommandsExecuted ?? []) {
-				if (!this._executedCommands.has(cmd)) {
-					this._pendingCommands.add(cmd);
-				}
-			}
-		}
-
-		this._pendingModes = new Set<string>();
-		for (const tip of tips) {
-			for (const mode of tip.excludeWhenModesUsed ?? []) {
-				if (!this._usedModes.has(mode)) {
-					this._pendingModes.add(mode);
-				}
-			}
-		}
-
-		this._pendingTools = new Set<string>();
-		for (const tip of tips) {
-			for (const toolId of tip.excludeWhenToolsInvoked ?? []) {
-				if (!this._invokedTools.has(toolId)) {
-					this._pendingTools.add(toolId);
-				}
-			}
-		}
-
-		// --- Set up command listener (auto-disposes when all seen) --------------
-
-		if (this._pendingCommands.size > 0) {
-			this._commandListener.value = commandService.onDidExecuteCommand(e => {
-				this.recordCommandExecuted(e.commandId);
-			});
-		}
-
-		// --- Set up tool listener (auto-disposes when all seen) -----------------
-
-		if (this._pendingTools.size > 0) {
-			this._toolListener.value = this._languageModelToolsService.onDidInvokeTool(e => {
-				// Track explicit tool IDs
-				if (this._pendingTools.has(e.toolId)) {
-					this._invokedTools.add(e.toolId);
-					this._pendingTools.delete(e.toolId);
-
-					this._persistSet(TipEligibilityTracker._TOOLS_STORAGE_KEY, this._invokedTools);
-				}
-
-				if (this._pendingTools.size === 0) {
-					this._toolListener.clear();
-				}
-			});
-		}
-
-		// --- Async file checks -------------------------------------------------
-
-		this._tipsWithFileExclusions = tips.filter(t => t.excludeWhenPromptFilesExist);
-		for (const tip of this._tipsWithFileExclusions) {
-			if (tip.excludeWhenPromptFilesExist!.excludeUntilChecked) {
-				this._excludedByFiles.add(tip.id);
-			}
-			this._checkForPromptFiles(tip);
-		}
-
-		// Re-check agent file exclusions when custom agents change (covers late discovery)
-		this._register(this._promptsService.onDidChangeCustomAgents(() => {
-			for (const tip of this._tipsWithFileExclusions) {
-				if (tip.excludeWhenPromptFilesExist!.promptType === PromptsType.agent) {
-					this._checkForPromptFiles(tip);
-				}
-			}
-		}));
-	}
-
-	recordCommandExecuted(commandId: string): void {
-		if (!this._pendingCommands.has(commandId)) {
-			return;
-		}
-
-		this._executedCommands.add(commandId);
-		this._persistSet(TipEligibilityTracker._COMMANDS_STORAGE_KEY, this._executedCommands);
-		this._pendingCommands.delete(commandId);
-
-		if (this._pendingCommands.size === 0) {
-			this._commandListener.clear();
-		}
-	}
-
-	/**
-	 * Records the current chat mode (kind + name) so future tip eligibility
-	 * checks can exclude mode-related tips. No-ops once all tracked modes
-	 * have been observed.
-	 */
-	recordCurrentMode(contextKeyService: IContextKeyService): void {
-		if (this._pendingModes.size === 0) {
-			return;
-		}
-
-		let changed = false;
-		const kind = contextKeyService.getContextKeyValue<string>(ChatContextKeys.chatModeKind.key);
-		if (kind && !this._usedModes.has(kind)) {
-			this._usedModes.add(kind);
-			this._pendingModes.delete(kind);
-			changed = true;
-		}
-		const name = contextKeyService.getContextKeyValue<string>(ChatContextKeys.chatModeName.key);
-		if (name && !this._usedModes.has(name)) {
-			this._usedModes.add(name);
-			this._pendingModes.delete(name);
-			changed = true;
-		}
-		if (changed) {
-			this._persistSet(TipEligibilityTracker._MODES_STORAGE_KEY, this._usedModes);
-		}
-	}
-
-	/**
-	 * Returns `true` when the tip should be **excluded** from the eligible set.
-	 */
-	isExcluded(tip: ITipDefinition): boolean {
-		if (tip.excludeWhenCommandsExecuted) {
-			for (const cmd of tip.excludeWhenCommandsExecuted) {
-				if (this._executedCommands.has(cmd)) {
-					this._logService.debug('#ChatTips: tip excluded because command was executed', tip.id, cmd);
-					return true;
-				}
-			}
-		}
-		if (tip.excludeWhenModesUsed) {
-			for (const mode of tip.excludeWhenModesUsed) {
-				if (this._usedModes.has(mode)) {
-					this._logService.debug('#ChatTips: tip excluded because mode was used', tip.id, mode);
-					return true;
-				}
-			}
-		}
-		if (tip.excludeWhenToolsInvoked) {
-			for (const toolId of tip.excludeWhenToolsInvoked) {
-				if (this._invokedTools.has(toolId)) {
-					this._logService.debug('#ChatTips: tip excluded because tool was invoked', tip.id, toolId);
-					return true;
-				}
-			}
-		}
-		if (tip.excludeWhenPromptFilesExist && this._excludedByFiles.has(tip.id)) {
-			this._logService.debug('#ChatTips: tip excluded because prompt files exist', tip.id);
-			return true;
-		}
-		return false;
-	}
-
-	/**
-	 * Revalidates all file-based tip exclusions. Tips with `excludeUntilChecked`
-	 * are conservatively hidden until the re-check completes.
-	 */
-	refreshPromptFileExclusions(): void {
-		for (const tip of this._tipsWithFileExclusions) {
-			if (tip.excludeWhenPromptFilesExist!.excludeUntilChecked) {
-				this._excludedByFiles.add(tip.id);
-			}
-			this._checkForPromptFiles(tip);
-		}
-	}
-
-	private async _checkForPromptFiles(tip: ITipDefinition): Promise<void> {
-		const inFlight = this._fileChecksInFlight.get(tip.id);
-		if (inFlight) {
-			await inFlight;
-			return;
-		}
-
-		const checkPromise = this._doCheckForPromptFiles(tip);
-		this._fileChecksInFlight.set(tip.id, checkPromise);
-		try {
-			await checkPromise;
-		} finally {
-			if (this._fileChecksInFlight.get(tip.id) === checkPromise) {
-				this._fileChecksInFlight.delete(tip.id);
-			}
-		}
-	}
-
-	private async _doCheckForPromptFiles(tip: ITipDefinition): Promise<void> {
-		const config = tip.excludeWhenPromptFilesExist!;
-		const generation = (this._fileCheckGeneration.get(tip.id) ?? 0) + 1;
-		this._fileCheckGeneration.set(tip.id, generation);
-
-		try {
-			const [promptFiles, agentInstructions] = await Promise.all([
-				this._promptsService.listPromptFiles(config.promptType, CancellationToken.None),
-				config.agentFileType ? this._promptsService.listAgentInstructions(CancellationToken.None) : Promise.resolve([]),
-			]);
-
-			// Discard stale result if a newer check was started while we were awaiting
-			if (this._fileCheckGeneration.get(tip.id) !== generation) {
-				return;
-			}
-
-			const hasPromptFiles = promptFiles.length > 0;
-			const hasAgentFile = config.agentFileType
-				? agentInstructions.some(f => f.type === config.agentFileType)
-				: false;
-			const hasPromptFilesOrAgentFile = hasPromptFiles || hasAgentFile;
-
-			if (hasPromptFilesOrAgentFile) {
-				this._excludedByFiles.add(tip.id);
-			} else {
-				this._excludedByFiles.delete(tip.id);
-			}
-		} catch {
-			if (this._fileCheckGeneration.get(tip.id) !== generation) {
-				return;
-			}
-			if (config.excludeUntilChecked) {
-				this._excludedByFiles.add(tip.id);
-			}
-		}
-	}
-
-	private _persistSet(key: string, set: Set<string>): void {
-		this._storageService.store(key, JSON.stringify([...set]), StorageScope.APPLICATION, StorageTarget.MACHINE);
-	}
-
-	private _readApplicationWithProfileFallback(key: string): string | undefined {
-		const applicationValue = this._storageService.get(key, StorageScope.APPLICATION);
-		if (applicationValue) {
-			return applicationValue;
-		}
-
-		const profileValue = this._storageService.get(key, StorageScope.PROFILE);
-		if (profileValue) {
-			this._storageService.store(key, profileValue, StorageScope.APPLICATION, StorageTarget.MACHINE);
-		}
-
-		return profileValue;
-	}
-}
+// Re-export types for backwards compatibility
+export type { ITipDefinition } from './chatTipCatalog.js';
+export { TipEligibilityTracker } from './chatTipEligibilityTracker.js';
 
 export class ChatTipService extends Disposable implements IChatTipService {
 	readonly _serviceBrand: undefined;
@@ -664,10 +178,7 @@ export class ChatTipService extends Disposable implements IChatTipService {
 	 */
 	private _contextKeyService: IContextKeyService | undefined;
 
-	private static readonly _DISMISSED_TIP_KEY = 'chat.tip.dismissed';
-	private static readonly _LAST_TIP_ID_KEY = 'chat.tip.lastTipId';
-	private static readonly _YOLO_EVER_ENABLED_KEY = 'chat.tip.yoloModeEverEnabled';
-	private static readonly _THINKING_PHRASES_EVER_MODIFIED_KEY = 'chat.tip.thinkingPhrasesEverModified';
+
 	private readonly _tracker: TipEligibilityTracker;
 	private readonly _createSlashCommandsUsageTracker: CreateSlashCommandsUsageTracker;
 	private _yoloModeEverEnabled: boolean;
@@ -684,6 +195,7 @@ export class ChatTipService extends Disposable implements IChatTipService {
 		@IChatEntitlementService private readonly _chatEntitlementService: IChatEntitlementService,
 		@ICommandService private readonly _commandService: ICommandService,
 		@ITelemetryService private readonly _telemetryService: ITelemetryService,
+		@IKeybindingService private readonly _keybindingService: IKeybindingService,
 	) {
 		super();
 		this._tracker = this._register(instantiationService.createInstance(TipEligibilityTracker, TIP_CATALOG));
@@ -701,7 +213,7 @@ export class ChatTipService extends Disposable implements IChatTipService {
 			}
 
 			if (this._hasFileOrFolderReference(message)) {
-				this._tracker.recordCommandExecuted(ATTACH_FILES_REFERENCE_TRACKING_COMMAND);
+				this._tracker.recordCommandExecuted(TipTrackingCommands.AttachFilesReferenceUsed);
 			}
 
 			const createCommandTrackingId = this._getCreateSlashCommandTrackingId(message);
@@ -711,10 +223,10 @@ export class ChatTipService extends Disposable implements IChatTipService {
 		}));
 
 		// Track whether yolo mode was ever enabled
-		this._yoloModeEverEnabled = this._storageService.getBoolean(ChatTipService._YOLO_EVER_ENABLED_KEY, StorageScope.APPLICATION, false);
+		this._yoloModeEverEnabled = this._storageService.getBoolean(ChatTipStorageKeys.YoloModeEverEnabled, StorageScope.APPLICATION, false);
 		if (!this._yoloModeEverEnabled && this._configurationService.getValue<boolean>(ChatConfiguration.GlobalAutoApprove)) {
 			this._yoloModeEverEnabled = true;
-			this._storageService.store(ChatTipService._YOLO_EVER_ENABLED_KEY, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
+			this._storageService.store(ChatTipStorageKeys.YoloModeEverEnabled, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
 		}
 		if (!this._yoloModeEverEnabled) {
 			const configListener = this._register(new MutableDisposable());
@@ -722,23 +234,23 @@ export class ChatTipService extends Disposable implements IChatTipService {
 				if (e.affectsConfiguration(ChatConfiguration.GlobalAutoApprove)) {
 					if (this._configurationService.getValue<boolean>(ChatConfiguration.GlobalAutoApprove)) {
 						this._yoloModeEverEnabled = true;
-						this._storageService.store(ChatTipService._YOLO_EVER_ENABLED_KEY, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
+						this._storageService.store(ChatTipStorageKeys.YoloModeEverEnabled, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
 						configListener.clear();
 					}
 				}
 			});
 		}
 
-		this._thinkingPhrasesEverModified = this._storageService.getBoolean(ChatTipService._THINKING_PHRASES_EVER_MODIFIED_KEY, StorageScope.APPLICATION, false);
+		this._thinkingPhrasesEverModified = this._storageService.getBoolean(ChatTipStorageKeys.ThinkingPhrasesEverModified, StorageScope.APPLICATION, false);
 		if (!this._thinkingPhrasesEverModified && this._isSettingModified(ChatConfiguration.ThinkingPhrases)) {
 			this._thinkingPhrasesEverModified = true;
-			this._storageService.store(ChatTipService._THINKING_PHRASES_EVER_MODIFIED_KEY, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
+			this._storageService.store(ChatTipStorageKeys.ThinkingPhrasesEverModified, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
 		}
 		if (!this._thinkingPhrasesEverModified) {
 			this._register(this._configurationService.onDidChangeConfiguration(e => {
 				if (e.affectsConfiguration(ChatConfiguration.ThinkingPhrases)) {
 					this._thinkingPhrasesEverModified = true;
-					this._storageService.store(ChatTipService._THINKING_PHRASES_EVER_MODIFIED_KEY, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
+					this._storageService.store(ChatTipStorageKeys.ThinkingPhrasesEverModified, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
 				}
 			}));
 		}
@@ -794,7 +306,7 @@ export class ChatTipService extends Disposable implements IChatTipService {
 			this._logTipTelemetry(this._shownTip.id, 'dismissed');
 			const dismissed = new Set(this._getDismissedTipIds());
 			dismissed.add(this._shownTip.id);
-			this._storageService.store(ChatTipService._DISMISSED_TIP_KEY, JSON.stringify([...dismissed]), StorageScope.APPLICATION, StorageTarget.MACHINE);
+			this._storageService.store(ChatTipStorageKeys.DismissedTips, JSON.stringify([...dismissed]), StorageScope.APPLICATION, StorageTarget.MACHINE);
 		}
 		// Keep the current tip reference so callers can navigate relative to it
 		// (for example, dismiss -> next should mirror next/previous behavior).
@@ -803,8 +315,8 @@ export class ChatTipService extends Disposable implements IChatTipService {
 	}
 
 	clearDismissedTips(): void {
-		this._storageService.remove(ChatTipService._DISMISSED_TIP_KEY, StorageScope.APPLICATION);
-		this._storageService.remove(ChatTipService._DISMISSED_TIP_KEY, StorageScope.PROFILE);
+		this._storageService.remove(ChatTipStorageKeys.DismissedTips, StorageScope.APPLICATION);
+		this._storageService.remove(ChatTipStorageKeys.DismissedTips, StorageScope.PROFILE);
 		this._shownTip = undefined;
 		this._tipRequestId = undefined;
 		this._contextKeyService = undefined;
@@ -812,7 +324,7 @@ export class ChatTipService extends Disposable implements IChatTipService {
 	}
 
 	private _getDismissedTipIds(): string[] {
-		const raw = this._readApplicationWithProfileFallback(ChatTipService._DISMISSED_TIP_KEY);
+		const raw = this._readApplicationWithProfileFallback(ChatTipStorageKeys.DismissedTips);
 		if (!raw) {
 			return [];
 		}
@@ -898,7 +410,7 @@ export class ChatTipService extends Disposable implements IChatTipService {
 				const nextTip = this._findNextEligibleTip(this._shownTip.id, contextKeyService);
 				if (nextTip) {
 					this._shownTip = nextTip;
-					this._storageService.store(ChatTipService._LAST_TIP_ID_KEY, nextTip.id, StorageScope.APPLICATION, StorageTarget.USER);
+					this._storageService.store(ChatTipStorageKeys.LastTipId, nextTip.id, StorageScope.APPLICATION, StorageTarget.USER);
 					const tip = this._createTip(nextTip);
 					this._onDidNavigateTip.fire(tip);
 					return tip;
@@ -940,7 +452,7 @@ export class ChatTipService extends Disposable implements IChatTipService {
 		let selectedTip: ITipDefinition | undefined;
 
 		// Determine where to start in the catalog based on the last-shown tip.
-		const lastTipId = this._readApplicationWithProfileFallback(ChatTipService._LAST_TIP_ID_KEY);
+		const lastTipId = this._readApplicationWithProfileFallback(ChatTipStorageKeys.LastTipId);
 		const lastCatalogIndex = lastTipId ? TIP_CATALOG.findIndex(tip => tip.id === lastTipId) : -1;
 		const startIndex = lastCatalogIndex === -1 ? 0 : (lastCatalogIndex + 1) % TIP_CATALOG.length;
 
@@ -960,7 +472,7 @@ export class ChatTipService extends Disposable implements IChatTipService {
 		}
 
 		// Persist the selected tip id so the next use advances to the following one.
-		this._storageService.store(ChatTipService._LAST_TIP_ID_KEY, selectedTip.id, StorageScope.APPLICATION, StorageTarget.USER);
+		this._storageService.store(ChatTipStorageKeys.LastTipId, selectedTip.id, StorageScope.APPLICATION, StorageTarget.USER);
 
 		// Record that we've shown a tip this session
 		this._tipRequestId = sourceId;
@@ -986,6 +498,35 @@ export class ChatTipService extends Disposable implements IChatTipService {
 		return this._navigateTip(-1, this._contextKeyService);
 	}
 
+	getNextEligibleTip(): IChatTip | undefined {
+		if (!this._contextKeyService || !this._shownTip) {
+			return undefined;
+		}
+
+		this._createSlashCommandsUsageTracker.syncContextKey(this._contextKeyService);
+		const currentIndex = TIP_CATALOG.findIndex(t => t.id === this._shownTip!.id);
+		if (currentIndex === -1) {
+			return undefined;
+		}
+
+		const dismissedIds = new Set(this._getDismissedTipIds());
+		for (let i = 1; i < TIP_CATALOG.length; i++) {
+			const idx = (currentIndex + i) % TIP_CATALOG.length;
+			const candidate = TIP_CATALOG[idx];
+			if (!dismissedIds.has(candidate.id) && this._isEligible(candidate, this._contextKeyService)) {
+				// Found the next eligible tip - update state and return it
+				this._shownTip = candidate;
+				this._tipRequestId = 'welcome';
+				this._storageService.store(ChatTipStorageKeys.LastTipId, candidate.id, StorageScope.APPLICATION, StorageTarget.USER);
+				this._logTipTelemetry(candidate.id, 'shown');
+				this._trackTipCommandClicks(candidate);
+				return this._createTip(candidate);
+			}
+		}
+
+		return undefined;
+	}
+
 	hasMultipleTips(): boolean {
 		if (!this._contextKeyService) {
 			return false;
@@ -1011,7 +552,7 @@ export class ChatTipService extends Disposable implements IChatTipService {
 			this._logTipTelemetry(this._shownTip.id, direction === 1 ? 'navigateNext' : 'navigatePrevious');
 			this._shownTip = candidate;
 			this._tipRequestId = 'welcome';
-			this._storageService.store(ChatTipService._LAST_TIP_ID_KEY, candidate.id, StorageScope.APPLICATION, StorageTarget.USER);
+			this._storageService.store(ChatTipStorageKeys.LastTipId, candidate.id, StorageScope.APPLICATION, StorageTarget.USER);
 			this._logTipTelemetry(candidate.id, 'shown');
 			this._trackTipCommandClicks(candidate);
 			const tip = this._createTip(candidate);
@@ -1161,13 +702,23 @@ export class ChatTipService extends Disposable implements IChatTipService {
 	}
 
 	private _createTip(tipDef: ITipDefinition): IChatTip {
-		const markdown = new MarkdownString(tipDef.message, {
-			isTrusted: tipDef.enabledCommands ? { enabledCommands: tipDef.enabledCommands } : false,
+		// Build the tip message with dynamic keybindings and command labels
+		const ctx: ITipBuildContext = { keybindingService: this._keybindingService };
+		const rawMessage = tipDef.buildMessage(ctx);
+
+		// Add "Tip:" prefix once here, avoiding duplication in individual tip definitions
+		const prefixedMessage = localize('tipPrefix', "**Tip:** {0}", rawMessage.value);
+
+		// Auto-extract enabled commands from the built message
+		const enabledCommands = extractCommandIds(prefixedMessage);
+
+		const markdown = new MarkdownString(prefixedMessage, {
+			isTrusted: enabledCommands.length > 0 ? { enabledCommands } : false,
 		});
 		return {
 			id: tipDef.id,
 			content: markdown,
-			enabledCommands: tipDef.enabledCommands,
+			enabledCommands,
 		};
 	}
 
@@ -1181,10 +732,16 @@ export class ChatTipService extends Disposable implements IChatTipService {
 
 	private _trackTipCommandClicks(tip: ITipDefinition): void {
 		this._tipCommandListener.clear();
-		if (!tip.enabledCommands?.length) {
+
+		// Build message to extract enabled commands dynamically
+		const ctx: ITipBuildContext = { keybindingService: this._keybindingService };
+		const rawMessage = tip.buildMessage(ctx);
+		const enabledCommands = extractCommandIds(rawMessage.value);
+
+		if (!enabledCommands.length) {
 			return;
 		}
-		const enabledCommandSet = new Set(tip.enabledCommands);
+		const enabledCommandSet = new Set(enabledCommands);
 		const dismissCommandSet = new Set(tip.dismissWhenCommandsClicked);
 		this._tipCommandListener.value = this._commandService.onDidExecuteCommand(e => {
 			if (enabledCommandSet.has(e.commandId) && this._shownTip?.id === tip.id) {
diff --git a/src/vs/workbench/contrib/chat/browser/chatTipStorageKeys.ts b/src/vs/workbench/contrib/chat/browser/chatTipStorageKeys.ts
new file mode 100644
index 0000000000000..1b7a995f8c86b
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/chatTipStorageKeys.ts
@@ -0,0 +1,48 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+/**
+ * Storage keys used by ChatTipService for persisting tip state.
+ */
+export const ChatTipStorageKeys = {
+	/** IDs of tips that have been permanently dismissed by the user. */
+	DismissedTips: 'chat.tip.dismissed',
+	/** The ID of the last tip that was shown, for round-robin selection. */
+	LastTipId: 'chat.tip.lastTipId',
+	/** Whether the user has ever enabled global auto-approve (yolo mode). */
+	YoloModeEverEnabled: 'chat.tip.yoloModeEverEnabled',
+	/** Whether the user has ever modified the thinking phrases setting. */
+	ThinkingPhrasesEverModified: 'chat.tip.thinkingPhrasesEverModified',
+};
+
+/**
+ * Storage keys used by TipEligibilityTracker for tracking user signals.
+ */
+export const TipEligibilityStorageKeys = {
+	/** Command IDs that have been executed (for excludeWhenCommandsExecuted). */
+	ExecutedCommands: 'chat.tips.executedCommands',
+	/** Chat modes that have been used (for excludeWhenModesUsed). */
+	UsedModes: 'chat.tips.usedModes',
+	/** Tool IDs that have been invoked (for excludeWhenToolsInvoked). */
+	InvokedTools: 'chat.tips.invokedTools',
+};
+
+/**
+ * Synthetic command IDs used to track user actions that don't have real commands.
+ * These are recorded when the user performs the action, allowing tips to be excluded
+ * via excludeWhenCommandsExecuted.
+ */
+export const TipTrackingCommands = {
+	/** Tracked when user attaches a file/folder reference with #. */
+	AttachFilesReferenceUsed: 'chat.tips.attachFiles.referenceUsed',
+	/** Tracked when user executes /create-instructions. */
+	CreateAgentInstructionsUsed: 'chat.tips.createAgentInstructions.commandUsed',
+	/** Tracked when user executes /create-prompt. */
+	CreatePromptUsed: 'chat.tips.createPrompt.commandUsed',
+	/** Tracked when user executes /create-agent. */
+	CreateAgentUsed: 'chat.tips.createAgent.commandUsed',
+	/** Tracked when user executes /create-skill. */
+	CreateSkillUsed: 'chat.tips.createSkill.commandUsed',
+} as const;
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatQuestionCarouselPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatQuestionCarouselPart.ts
index 13931c98e94f8..ddd912f7c0c55 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatQuestionCarouselPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatQuestionCarouselPart.ts
@@ -489,11 +489,10 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 		// Render question header row with title and close button
 		const headerRow = dom.$('.chat-question-header-row');
 
-		// Render question message with title styling (no progress prefix)
-		// Fall back to question.title if message is not provided
-		const questionText = question.message ?? question.title;
-		if (questionText) {
+		// Render question title (short header) in the header bar as plain text
+		if (question.title) {
 			const title = dom.$('.chat-question-title');
+			const questionText = question.title;
 			const messageContent = this.getQuestionText(questionText);
 
 			title.setAttribute('aria-label', messageContent);
@@ -529,6 +528,18 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 
 		this._questionContainer.appendChild(headerRow);
 
+		// Render full question text below the header row (supports multi-line and markdown)
+		if (question.message) {
+			const messageEl = dom.$('.chat-question-message');
+			if (isMarkdownString(question.message)) {
+				const renderedMessage = questionRenderStore.add(this._markdownRendererService.render(MarkdownString.lift(question.message)));
+				messageEl.appendChild(renderedMessage.element);
+			} else {
+				messageEl.textContent = this.getQuestionText(question.message);
+			}
+			this._questionContainer.appendChild(messageEl);
+		}
+
 		const isSingleQuestion = this.carousel.questions.length === 1;
 		// Update step indicator in footer
 		if (this._stepIndicator) {
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatTipContentPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatTipContentPart.ts
index 892ed35e18d20..75ac2bef68ec2 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatTipContentPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatTipContentPart.ts
@@ -74,7 +74,9 @@ export class ChatTipContentPart extends Disposable {
 		this._renderTip(tip);
 
 		this._register(this._chatTipService.onDidDismissTip(() => {
-			const nextTip = this._chatTipService.navigateToNextTip();
+			// Use getNextEligibleTip instead of navigateToNextTip to show the next
+			// available tip even if it's the only one left (no multiple-tip requirement)
+			const nextTip = this._chatTipService.getNextEligibleTip();
 			if (nextTip) {
 				this._renderTip(nextTip);
 				dom.runAtThisOrScheduleAtNextAnimationFrame(dom.getWindow(this.domNode), () => this.focus());
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatQuestionCarousel.css b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatQuestionCarousel.css
index 18a456c7fbb17..9407257b4789c 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatQuestionCarousel.css
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatQuestionCarousel.css
@@ -43,38 +43,44 @@
 
 	.chat-question-header-row {
 		display: flex;
-		justify-content: space-between;
-		align-items: center;
-		gap: 8px;
-		min-width: 0;
-		padding-bottom: 5px;
-		margin-left: -16px;
-		margin-right: -16px;
-		padding-left: 16px;
-		padding-right: 16px;
-		border-bottom: 1px solid var(--vscode-chat-requestBorder);
+		flex-direction: column;
+		background: var(--vscode-chat-requestBackground);
+		padding: 0 16px 10px 16px;
+		overflow: hidden;
 
 		.chat-question-title {
 			flex: 1;
 			min-width: 0;
-			word-wrap: break-word;
-			overflow-wrap: break-word;
-			font-weight: 500;
-			font-size: var(--vscode-chat-font-size-body-s);
-			margin: 0;
+			padding-top: 4px;
+			padding-bottom: 4px;
+			margin-left: -16px;
+			margin-right: -16px;
+			padding-left: 16px;
+			padding-right: 16px;
+			border-bottom: 1px solid var(--vscode-chat-requestBorder);
+
+			.chat-question-title {
+				flex: 1;
+				min-width: 0;
+				word-wrap: break-word;
+				overflow-wrap: break-word;
+				font-weight: 500;
+				font-size: var(--vscode-chat-font-size-body-s);
+				margin: 0;
 
-			.rendered-markdown {
-				a {
-					color: var(--vscode-textLink-foreground);
-				}
+				.rendered-markdown {
+					a {
+						color: var(--vscode-textLink-foreground);
+					}
 
-				a:hover,
-				a:active {
-					color: var(--vscode-textLink-activeForeground);
-				}
+					a:hover,
+					a:active {
+						color: var(--vscode-textLink-activeForeground);
+					}
 
-				p {
-					margin: 0;
+					p {
+						margin: 0;
+					}
 				}
 			}
 
@@ -105,6 +111,29 @@
 				background: var(--vscode-toolbar-hoverBackground) !important;
 			}
 		}
+
+		.chat-question-message {
+			padding-top: 8px;
+			font-size: var(--vscode-chat-font-size-body-s);
+			word-wrap: break-word;
+			overflow-wrap: break-word;
+			line-height: 1.4;
+
+			.rendered-markdown {
+				a {
+					color: var(--vscode-textLink-foreground);
+				}
+
+				a:hover,
+				a:active {
+					color: var(--vscode-textLink-activeForeground);
+				}
+
+				p {
+					margin: 0;
+				}
+			}
+		}
 	}
 }
 
@@ -142,7 +171,7 @@
 
 		.chat-question-list-item {
 			display: flex;
-			align-items: center;
+			align-items: flex-start;
 			gap: 8px;
 			padding: 3px 8px;
 			cursor: pointer;
@@ -167,9 +196,9 @@
 			.chat-question-list-label {
 				font-size: var(--vscode-chat-font-size-body-s);
 				flex: 1;
-				overflow: hidden;
-				text-overflow: ellipsis;
-				white-space: nowrap;
+				word-wrap: break-word;
+				overflow-wrap: break-word;
+				padding-top: 2px;
 			}
 
 			.chat-question-list-label-title {
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatTerminalToolProgressPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatTerminalToolProgressPart.ts
index d864ae17d5a2a..4fc2868f40fb2 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatTerminalToolProgressPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatTerminalToolProgressPart.ts
@@ -57,9 +57,36 @@ import { PANEL_BACKGROUND } from '../../../../../../common/theme.js';
 import { editorBackground } from '../../../../../../../platform/theme/common/colorRegistry.js';
 import { IThemeService } from '../../../../../../../platform/theme/common/themeService.js';
 
+/**
+ * Minimum number of rows to display in the terminal output view.
+ */
 const MIN_OUTPUT_ROWS = 1;
+
+/**
+ * Maximum number of rows to display in the terminal output view before scrolling.
+ */
 const MAX_OUTPUT_ROWS = 10;
 
+/**
+ * Maximum number of characters to display in the command title before truncating.
+ */
+const MAX_COMMAND_TITLE_LENGTH = 50;
+
+/**
+ * Maximum number of retries when waiting for terminal output to appear.
+ */
+const MAX_OUTPUT_POLL_RETRIES = 10;
+
+/**
+ * Delay between retries when polling for terminal output (in milliseconds).
+ */
+const OUTPUT_POLL_DELAY_MS = 100;
+
+/**
+ * Minimum number of data events that indicate real output (vs shell integration sequences).
+ */
+const MIN_DATA_EVENTS_FOR_REAL_OUTPUT = 2;
+
 /**
  * Remembers whether a tool invocation was last expanded so state survives virtualization re-renders.
  */
@@ -196,6 +223,25 @@ class TerminalCommandDecoration extends Disposable {
 	}
 }
 
+/**
+ * A chat content part that displays terminal tool invocation progress.
+ *
+ * This component shows:
+ * - The command being executed with syntax highlighting
+ * - A status decoration indicating success/failure/running state
+ * - Expandable terminal output with live streaming support
+ * - Actions to focus the terminal, show/hide output, and continue in background
+ *
+ * The component supports two rendering modes:
+ * - Standard mode: Shows full progress with status indicators
+ * - Collapsible wrapper mode: For thinking containers with simplified UI
+ *
+ * Output auto-expansion behavior:
+ * - Long-running commands with output auto-expand after a short delay
+ * - Fast commands that complete quickly don't auto-expand (prevents flickering)
+ * - Failed commands can be configured to auto-expand via settings
+ * - Successful commands auto-collapse if output was auto-expanded
+ */
 export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart implements IChatTerminalToolProgressPart {
 	public readonly domNode: HTMLElement;
 
@@ -393,9 +439,8 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 
 	private _createCollapsibleWrapper(contentElement: HTMLElement, commandText: string, toolInvocation: IChatToolInvocation | IChatToolInvocationSerialized, context: IChatContentPartRenderContext): HTMLElement {
 		// truncate header when it's too long
-		const maxCommandLength = 50;
-		const truncatedCommand = commandText.length > maxCommandLength
-			? commandText.substring(0, maxCommandLength) + '...'
+		const truncatedCommand = commandText.length > MAX_COMMAND_TITLE_LENGTH
+			? commandText.substring(0, MAX_COMMAND_TITLE_LENGTH) + '...'
 			: commandText;
 
 		const isComplete = IChatToolInvocation.isComplete(toolInvocation);
@@ -597,6 +642,27 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 		this._decoration.update();
 	}
 
+	/**
+	 * Determines whether the terminal output should auto-expand.
+	 * Returns false if already expanded, user has manually toggled, component is disposed,
+	 * or if the invocation was previously expanded (to preserve state across re-renders).
+	 */
+	private _shouldAutoExpand(): boolean {
+		return !this._outputView.isExpanded &&
+			!this._userToggledOutput &&
+			!this._store.isDisposed &&
+			!expandedStateByInvocation.get(this.toolInvocation);
+	}
+
+	/**
+	 * Registers event listeners on the terminal instance to track command execution,
+	 * manage auto-expansion of output, and handle command completion.
+	 *
+	 * This method sets up:
+	 * - Command detection listeners for tracking command lifecycle
+	 * - Auto-expand logic based on command output and duration
+	 * - Instance disposal handling to clean up actions and state
+	 */
 	private _registerInstanceListener(terminalInstance: ITerminalInstance): void {
 		const commandDetectionListener = this._register(new MutableDisposable<IDisposable>());
 		const tryResolveCommand = async (): Promise<ITerminalCommand | undefined> => {
@@ -637,14 +703,14 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 				// hasn't moved past the marker (e.g., progress bars updating on same line)
 				// Shell integration sequences fire a couple times per command (PromptStart, CommandStart,
 				// CommandExecuted), so we need a small threshold to filter those out
-				return receivedDataCount > 2;
+				return receivedDataCount > MIN_DATA_EVENTS_FOR_REAL_OUTPUT;
 			};
 
 			// Use the extracted auto-expand logic
 			const autoExpand = store.add(new TerminalToolAutoExpand({
 				commandDetection,
 				onWillData: terminalInstance.onWillData,
-				shouldAutoExpand: () => !this._outputView.isExpanded && !this._userToggledOutput && !this._store.isDisposed && !expandedStateByInvocation.get(this.toolInvocation),
+				shouldAutoExpand: () => this._shouldAutoExpand(),
 				hasRealOutput,
 			}));
 			store.add(autoExpand.onDidRequestExpand(() => {
@@ -667,18 +733,8 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 				this._addActions(terminalInstance, this._terminalData.terminalToolSessionId);
 				const resolvedCommand = this._getResolvedCommand(terminalInstance);
 
-				// update title
-				this.markCollapsibleWrapperComplete();
+				this._handleCommandCompletion(resolvedCommand);
 
-				// Auto-collapse on success
-				if (resolvedCommand?.exitCode === 0 && this._outputView.isExpanded && !this._userToggledOutput) {
-					this._toggleOutput(false);
-				}
-				// keep outer wrapper expanded on error
-				const autoExpandFailures = this._configurationService.getValue<boolean>(ChatConfiguration.AutoExpandToolFailures);
-				if (autoExpandFailures && resolvedCommand?.exitCode !== undefined && resolvedCommand.exitCode !== 0 && this._thinkingCollapsibleWrapper) {
-					this.expandCollapsibleWrapper();
-				}
 				if (resolvedCommand?.endMarker) {
 					commandDetectionListener.clear();
 				}
@@ -688,17 +744,7 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 			const resolvedImmediately = await tryResolveCommand();
 			if (resolvedImmediately?.endMarker) {
 				commandDetectionListener.clear();
-				// update title
-				this.markCollapsibleWrapperComplete();
-				// Auto-collapse on success
-				if (resolvedImmediately.exitCode === 0 && this._outputView.isExpanded && !this._userToggledOutput) {
-					this._toggleOutput(false);
-				}
-				// keep outer wrapper expanded on error
-				const autoExpandFailures = this._configurationService.getValue<boolean>(ChatConfiguration.AutoExpandToolFailures);
-				if (autoExpandFailures && resolvedImmediately.exitCode !== undefined && resolvedImmediately.exitCode !== 0 && this._thinkingCollapsibleWrapper) {
-					this.expandCollapsibleWrapper();
-				}
+				this._handleCommandCompletion(resolvedImmediately);
 				return;
 			}
 		};
@@ -753,6 +799,29 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 		this._continueInBackgroundAction.clear();
 	}
 
+	/**
+	 * Handles the completion of a terminal command by updating the UI state.
+	 * This includes marking the collapsible wrapper as complete, auto-collapsing
+	 * successful commands, and keeping failed commands expanded.
+	 *
+	 * @param resolvedCommand The completed terminal command with exit code information.
+	 */
+	private _handleCommandCompletion(resolvedCommand: ITerminalCommand | undefined): void {
+		// Update title to show completion state
+		this.markCollapsibleWrapperComplete();
+
+		// Auto-collapse on success (exit code 0)
+		if (resolvedCommand?.exitCode === 0 && this._outputView.isExpanded && !this._userToggledOutput) {
+			this._toggleOutput(false);
+		}
+
+		// Keep outer wrapper expanded on error for visibility
+		const autoExpandFailures = this._configurationService.getValue<boolean>(ChatConfiguration.AutoExpandToolFailures);
+		if (autoExpandFailures && resolvedCommand?.exitCode !== undefined && resolvedCommand.exitCode !== 0 && this._thinkingCollapsibleWrapper) {
+			this.expandCollapsibleWrapper();
+		}
+	}
+
 	private async _toggleOutput(expanded: boolean): Promise<boolean> {
 		const didChange = await this._outputView.toggle(expanded);
 		const isExpanded = this._outputView.isExpanded;
@@ -877,6 +946,21 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 	}
 }
 
+/**
+ * A component that displays terminal command output in an expandable/collapsible section.
+ *
+ * This component supports two modes of displaying output:
+ * - **Live output**: Mirrors the output from a running terminal instance in real-time,
+ *   supporting streaming updates, scroll-lock behavior, and user input forwarding.
+ * - **Snapshot output**: Displays a static snapshot of previously captured terminal output,
+ *   useful for serialized/restored chat sessions.
+ *
+ * Features:
+ * - Automatic height calculation based on line count (min/max row limits)
+ * - Scroll-lock behavior: stays at bottom during streaming, respects user scroll position
+ * - Accessibility: proper ARIA labels and accessible view support
+ * - Theme-aware background color that adapts to panel vs editor context
+ */
 class ChatTerminalToolOutputSection extends Disposable {
 	public readonly domNode: HTMLElement;
 
@@ -1130,9 +1214,8 @@ class ChatTerminalToolOutputSection extends Disposable {
 		// 1. Command is running but executedMarker isn't set yet (renderCommand returns undefined)
 		// 2. Command finished quickly but buffer isn't ready yet
 		if (!hasOutput) {
-			const maxRetries = 10;
-			for (let retry = 0; retry < maxRetries && !hasOutput; retry++) {
-				await timeout(100);
+			for (let retry = 0; retry < MAX_OUTPUT_POLL_RETRIES && !hasOutput; retry++) {
+				await timeout(OUTPUT_POLL_DELAY_MS);
 				if (this._store.isDisposed) {
 					return true;
 				}
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/chatModelPicker.ts b/src/vs/workbench/contrib/chat/browser/widget/input/chatModelPicker.ts
index 2eb6414caed91..d6a3689597bac 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/input/chatModelPicker.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/chatModelPicker.ts
@@ -266,7 +266,6 @@ export function buildModelPickerItems(
 		}
 
 		// Render promoted section: available first, then sorted alphabetically by name
-		let hasShownActionLink = false;
 		if (promotedItems.length > 0) {
 			promotedItems.sort((a, b) => {
 				const aAvail = a.kind === 'available' ? 0 : 1;
@@ -283,11 +282,7 @@ export function buildModelPickerItems(
 				if (item.kind === 'available') {
 					items.push(createModelItem(createModelAction(item.model, selectedModelId, onSelect), item.model));
 				} else {
-					const showActionLink = item.reason === 'upgrade' ? !hasShownActionLink : true;
-					if (showActionLink && item.reason === 'upgrade') {
-						hasShownActionLink = true;
-					}
-					items.push(createUnavailableModelItem(item.id, item.entry, item.reason, manageSettingsUrl, updateStateType, undefined, showActionLink));
+					items.push(createUnavailableModelItem(item.id, item.entry, item.reason, manageSettingsUrl, updateStateType));
 				}
 			}
 		}
@@ -336,7 +331,7 @@ export function buildModelPickerItems(
 			for (const model of otherModels) {
 				const entry = controlModels[model.metadata.id] ?? controlModels[model.identifier];
 				if (entry?.minVSCodeVersion && !isVersionAtLeast(currentVSCodeVersion, entry.minVSCodeVersion)) {
-					items.push(createUnavailableModelItem(model.metadata.id, entry, 'update', manageSettingsUrl, updateStateType, ModelPickerSection.Other, true));
+					items.push(createUnavailableModelItem(model.metadata.id, entry, 'update', manageSettingsUrl, updateStateType, ModelPickerSection.Other));
 				} else {
 					items.push(createModelItem(createModelAction(model, selectedModelId, onSelect, ModelPickerSection.Other), model));
 				}
@@ -398,14 +393,11 @@ function createUnavailableModelItem(
 	manageSettingsUrl: string | undefined,
 	updateStateType: StateType,
 	section?: string,
-	showActionLink: boolean = true,
 ): IActionListItem<IActionWidgetDropdownAction> {
 	let description: string | MarkdownString | undefined;
 
 	if (reason === 'upgrade') {
-		description = showActionLink
-			? new MarkdownString(localize('chat.modelPicker.upgradeLink', "[Upgrade your plan](command:workbench.action.chat.upgradePlan \" \")"), { isTrusted: true })
-			: undefined;
+		description = new MarkdownString(localize('chat.modelPicker.upgradeLink', "[Upgrade your plan](command:workbench.action.chat.upgradePlan \" \")"), { isTrusted: true });
 	} else if (reason === 'update') {
 		description = localize('chat.modelPicker.updateDescription', "Update VS Code");
 	} else {
diff --git a/src/vs/workbench/contrib/chat/test/browser/chatTipService.test.ts b/src/vs/workbench/contrib/chat/test/browser/chatTipService.test.ts
index 814c6c740b9ab..ba43aa820ee2c 100644
--- a/src/vs/workbench/contrib/chat/test/browser/chatTipService.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/chatTipService.test.ts
@@ -5,12 +5,14 @@
 
 import assert from 'assert';
 import { Emitter, Event } from '../../../../../base/common/event.js';
+import { MarkdownString } from '../../../../../base/common/htmlContent.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
 import { ICommandEvent, ICommandService } from '../../../../../platform/commands/common/commands.js';
 import { ConfigurationTarget, IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
 import { TestConfigurationService } from '../../../../../platform/configuration/test/common/testConfigurationService.js';
 import { ContextKeyExpression, IContextKeyService } from '../../../../../platform/contextkey/common/contextkey.js';
 import { TestInstantiationService } from '../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
+import { IKeybindingService } from '../../../../../platform/keybinding/common/keybinding.js';
 import { MockContextKeyService } from '../../../../../platform/keybinding/test/common/mockKeybindingService.js';
 import { ILogService, NullLogService } from '../../../../../platform/log/common/log.js';
 import { IProductService } from '../../../../../platform/product/common/productService.js';
@@ -80,6 +82,18 @@ suite('ChatTipService', () => {
 		return testDisposables.add(instantiationService.createInstance(ChatTipService));
 	}
 
+	/**
+	 * Creates a mock ITipDefinition with a buildMessage function.
+	 * Tests can provide any ITipDefinition properties except buildMessage.
+	 */
+	function createMockTip(overrides: Omit<ITipDefinition, 'buildMessage'> & { message?: string }): ITipDefinition {
+		const { message, ...rest } = overrides;
+		return {
+			...rest,
+			buildMessage: () => new MarkdownString(message ?? 'test'),
+		};
+	}
+
 	setup(() => {
 		instantiationService = testDisposables.add(new TestInstantiationService());
 		contextKeyService = new MockContextKeyServiceWithRulesMatching();
@@ -107,6 +121,9 @@ suite('ChatTipService', () => {
 		instantiationService.stub(IChatEntitlementService, chatEntitlementService);
 		instantiationService.stub(IChatService, new MockChatService());
 		instantiationService.stub(ITelemetryService, NullTelemetryService);
+		instantiationService.stub(IKeybindingService, {
+			lookupKeybinding: () => undefined,
+		} as Partial<IKeybindingService> as IKeybindingService);
 	});
 
 	test('returns a welcome tip', () => {
@@ -323,6 +340,62 @@ suite('ChatTipService', () => {
 		}
 	});
 
+	test('getNextEligibleTip returns next tip even when only one remains', async () => {
+		const service = createService();
+
+		// Flush microtask queue so async file-check exclusions resolve
+		await new Promise<void>(r => queueMicrotask(r));
+
+		// Get the initial tip
+		const tip1 = service.getWelcomeTip(contextKeyService);
+		assert.ok(tip1, 'Should have an initial tip');
+
+		// Navigate to next tip
+		const tip2 = service.navigateToNextTip();
+		assert.ok(tip2, 'Should have a second tip');
+		assert.notStrictEqual(tip1.id, tip2.id, 'Second tip should be different');
+
+		// Dismiss all tips except tip1 by dismissing current tip and using getNextEligibleTip
+		const dismissedIds = new Set<string>();
+		dismissedIds.add(tip2.id);
+		service.dismissTip();
+
+		// Keep dismissing until we can't get any more tips
+		let nextTip = service.getNextEligibleTip();
+		while (nextTip && !dismissedIds.has(nextTip.id)) {
+			if (nextTip.id === tip1.id) {
+				// We found tip1 again - this is the expected behavior (bug fix verification)
+				break;
+			}
+			dismissedIds.add(nextTip.id);
+			service.dismissTip();
+			nextTip = service.getNextEligibleTip();
+		}
+
+		// The key assertion: getNextEligibleTip should return tip1 even if it's the only one left
+		assert.ok(nextTip, 'getNextEligibleTip should return the last remaining eligible tip');
+	});
+
+	test('getNextEligibleTip returns undefined when all tips are dismissed', async () => {
+		const service = createService();
+
+		// Flush microtask queue so async file-check exclusions resolve
+		await new Promise<void>(r => queueMicrotask(r));
+
+		// Dismiss all tips
+		for (let i = 0; i < 100; i++) {
+			const tip = service.getWelcomeTip(contextKeyService);
+			if (!tip) {
+				break;
+			}
+			service.dismissTip();
+		}
+
+		// After dismissing all, getNextEligibleTip should return undefined
+		const nextTip = service.getNextEligibleTip();
+		assert.strictEqual(nextTip, undefined, 'getNextEligibleTip should return undefined when all tips are dismissed');
+	});
+
 	test('dismissTip fires onDidDismissTip event', () => {
 		const service = createService();
 
@@ -448,11 +521,10 @@ suite('ChatTipService', () => {
 	}
 
 	test('excludes tip.undoChanges when restore checkpoint command has been executed', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.undoChanges',
-			message: 'test',
 			excludeWhenCommandsExecuted: ['workbench.action.chat.restoreCheckpoint'],
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -471,11 +543,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('persists executed command exclusions in application storage', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.undoChanges',
-			message: 'test',
 			excludeWhenCommandsExecuted: ['workbench.action.chat.restoreCheckpoint'],
-		};
+		});
 
 		testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -494,11 +565,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('migrates executed command exclusions from profile to application storage', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.undoChanges',
-			message: 'test',
 			excludeWhenCommandsExecuted: ['workbench.action.chat.restoreCheckpoint'],
-		};
+		});
 
 		storageService.store('chat.tips.executedCommands', JSON.stringify(['workbench.action.chat.restoreCheckpoint']), StorageScope.PROFILE, StorageTarget.MACHINE);
 
@@ -516,11 +586,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('excludes tip.customInstructions when copilot-instructions.md exists in workspace', async () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.customInstructions',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.instructions, agentFileType: AgentFileType.copilotInstructionsMd, excludeUntilChecked: true },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -538,11 +607,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('does not exclude tip.customInstructions when only AGENTS.md exists', async () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.customInstructions',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.instructions, agentFileType: AgentFileType.copilotInstructionsMd, excludeUntilChecked: true },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -560,11 +628,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('excludes tip.customInstructions when .instructions.md files exist in workspace', async () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.customInstructions',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.instructions, agentFileType: AgentFileType.copilotInstructionsMd, excludeUntilChecked: true },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -582,11 +649,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('does not exclude tip.customInstructions when no instruction files exist', async () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.customInstructions',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.instructions, agentFileType: AgentFileType.copilotInstructionsMd, excludeUntilChecked: true },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -604,11 +670,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('excludes tip.customInstructions when generate instructions command has been executed', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.customInstructions',
-			message: 'test',
 			excludeWhenCommandsExecuted: [GENERATE_AGENT_INSTRUCTIONS_COMMAND_ID],
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -627,11 +692,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('excludes tip.agentMode when agent mode has been used in workspace', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.agentMode',
-			message: 'test',
 			excludeWhenModesUsed: [ChatModeKind.Agent],
-		};
+		});
 
 		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
 		contextKeyService.createKey(ChatContextKeys.chatModeName.key, 'Agent');
@@ -653,11 +717,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('excludes tip.planMode when Plan mode has been used in workspace', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.planMode',
-			message: 'test',
 			excludeWhenModesUsed: ['Plan'],
-		};
+		});
 
 		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
 		contextKeyService.createKey(ChatContextKeys.chatModeName.key, 'Plan');
@@ -679,11 +742,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('excludes tip.planMode when open plan command has been executed', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.planMode',
-			message: 'test',
 			excludeWhenCommandsExecuted: ['workbench.action.chat.openPlan'],
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -702,11 +764,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('persists command exclusions to workspace storage across tracker instances', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.undoChanges',
-			message: 'test',
 			excludeWhenCommandsExecuted: ['workbench.action.chat.restoreCheckpoint'],
-		};
+		});
 
 		const tracker1 = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -734,11 +795,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('persists mode exclusions to workspace storage across tracker instances', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.agentMode',
-			message: 'test',
 			excludeWhenModesUsed: [ChatModeKind.Agent],
-		};
+		});
 
 		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
 		contextKeyService.createKey(ChatContextKeys.chatModeName.key, 'Agent');
@@ -804,11 +864,10 @@ suite('ChatTipService', () => {
 
 	test('excludes tip when tracked tool has been invoked', () => {
 		const mockToolsService = createMockToolsService();
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.mermaid',
-			message: 'test',
 			excludeWhenToolsInvoked: ['renderMermaidDiagram'],
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -828,11 +887,10 @@ suite('ChatTipService', () => {
 
 	test('persists tool exclusions to workspace storage across tracker instances', () => {
 		const mockToolsService = createMockToolsService();
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.subagents',
-			message: 'test',
 			excludeWhenToolsInvoked: ['runSubagent'],
-		};
+		});
 
 		const tracker1 = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -860,11 +918,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('excludes tip.skill when skill files exist in workspace', async () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.skill',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.skill },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -882,11 +939,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('does not exclude tip.skill when no skill files exist', async () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.skill',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.skill },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -1268,11 +1324,10 @@ suite('ChatTipService', () => {
 		const agentChangeEmitter = testDisposables.add(new Emitter<void>());
 		let agentFiles: IPromptPath[] = [];
 
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.customAgent',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.agent, excludeUntilChecked: true },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -1301,11 +1356,10 @@ suite('ChatTipService', () => {
 	test('refreshPromptFileExclusions re-checks instruction files after startup', async () => {
 		let instructionFiles: IPromptPath[] = [];
 
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.customInstructions',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.instructions, agentFileType: AgentFileType.copilotInstructionsMd, excludeUntilChecked: true },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
diff --git a/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatQuestionCarouselPart.test.ts b/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatQuestionCarouselPart.test.ts
index 65d42852f534d..7fbf788530a3b 100644
--- a/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatQuestionCarouselPart.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatQuestionCarouselPart.test.ts
@@ -99,13 +99,15 @@ suite('ChatQuestionCarouselPart', () => {
 
 			const title = widget.domNode.querySelector('.chat-question-title');
 			assert.ok(title, 'title element should exist');
-			assert.ok(title?.querySelector('.rendered-markdown'), 'markdown content should be rendered');
-			assert.strictEqual(title?.textContent?.includes('**details**'), false, 'markdown syntax should not be shown as raw text');
-			const link = title?.querySelector('a') as HTMLAnchorElement | null;
+			const messageEl = widget.domNode.querySelector('.chat-question-message');
+			assert.ok(messageEl, 'message element should exist');
+			assert.ok(messageEl?.querySelector('.rendered-markdown'), 'markdown content should be rendered');
+			assert.strictEqual(messageEl?.textContent?.includes('**details**'), false, 'markdown syntax should not be shown as raw text');
+			const link = messageEl?.querySelector('a') as HTMLAnchorElement | null;
 			assert.ok(link, 'markdown link should render as anchor');
 		});
 
-		test('renders markdown in plain string question message', () => {
+		test('renders plain string question message as text', () => {
 			const carousel = createMockCarousel([
 				{
 					id: 'q1',
@@ -116,12 +118,10 @@ suite('ChatQuestionCarouselPart', () => {
 			]);
 			createWidget(carousel);
 
-			const title = widget.domNode.querySelector('.chat-question-title');
-			assert.ok(title, 'title element should exist');
-			assert.ok(title?.querySelector('.rendered-markdown'), 'markdown content should be rendered for plain string messages');
-			assert.strictEqual(title?.textContent?.includes('**details**'), false, 'markdown syntax should not be shown as raw text');
-			const link = title?.querySelector('a') as HTMLAnchorElement | null;
-			assert.ok(link, 'markdown link should render as anchor');
+			const messageEl = widget.domNode.querySelector('.chat-question-message');
+			assert.ok(messageEl, 'message element should exist');
+			assert.ok(messageEl?.textContent?.includes('details'), 'plain text content should be rendered');
+			assert.strictEqual(messageEl?.querySelector('.rendered-markdown'), null, 'plain string message should not use markdown renderer');
 		});
 
 		test('renders progress indicator correctly', () => {
diff --git a/src/vs/workbench/contrib/chat/test/browser/widget/input/chatModelPicker.test.ts b/src/vs/workbench/contrib/chat/test/browser/widget/input/chatModelPicker.test.ts
index b9d21246bba9c..d74122c7f6155 100644
--- a/src/vs/workbench/contrib/chat/test/browser/widget/input/chatModelPicker.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/widget/input/chatModelPicker.test.ts
@@ -580,7 +580,7 @@ suite('buildModelPickerItems', () => {
 		assert.strictEqual(unavailable.group?.icon?.id, Codicon.blank.id);
 	});
 
-	test('anonymous user sees upgrade description only on first unavailable model', () => {
+	test('anonymous user sees upgrade description on each unavailable model', () => {
 		const auto = createAutoModel();
 		const items = callBuild([auto], {
 			recentModelIds: ['model-a', 'model-b'],
@@ -596,10 +596,11 @@ suite('buildModelPickerItems', () => {
 		assert.strictEqual(disabledItems.length, 2);
 		assert.ok(disabledItems[0].description instanceof MarkdownString);
 		assert.ok(disabledItems[0].description.value.includes('Upgrade'));
-		assert.strictEqual(disabledItems[1].description, undefined);
+		assert.ok(disabledItems[1].description instanceof MarkdownString);
+		assert.ok(disabledItems[1].description.value.includes('Upgrade'));
 	});
 
-	test('free user sees upgrade description only on first unavailable model', () => {
+	test('free user sees upgrade description on each unavailable model', () => {
 		const auto = createAutoModel();
 		const items = callBuild([auto], {
 			recentModelIds: ['model-a', 'model-b'],
@@ -614,7 +615,8 @@ suite('buildModelPickerItems', () => {
 		assert.strictEqual(disabledItems.length, 2);
 		assert.ok(disabledItems[0].description instanceof MarkdownString);
 		assert.ok(disabledItems[0].description.value.includes('Upgrade'));
-		assert.strictEqual(disabledItems[1].description, undefined);
+		assert.ok(disabledItems[1].description instanceof MarkdownString);
+		assert.ok(disabledItems[1].description.value.includes('Upgrade'));
 	});
 
 	test('anonymous user model selection triggers onSelect normally', () => {
diff --git a/src/vs/workbench/services/themes/browser/cssExtensionPoint.ts b/src/vs/workbench/services/themes/browser/cssExtensionPoint.ts
index cdeca23bd2dd9..69b74111341b0 100644
--- a/src/vs/workbench/services/themes/browser/cssExtensionPoint.ts
+++ b/src/vs/workbench/services/themes/browser/cssExtensionPoint.ts
@@ -157,6 +157,10 @@ export class CSSExtensionPoint {
 				// Check if this extension's theme is currently active
 				if (this.isExtensionThemeActive(extensionId)) {
 					this.activateExtensionCSS(extension);
+				} else if (this.stylesheetsByExtension.has(extensionId)) {
+					// Theme is no longer active but cached CSS is still loaded — remove it
+					this.removeStylesheets(extensionId);
+					this.clearCacheForExtension(extensionId);
 				}
 			}
 		});
@@ -173,14 +177,17 @@ export class CSSExtensionPoint {
 	}
 
 	private onThemeChange(): void {
-		// Check all pending extensions and activate/deactivate as needed
+		// Activate pending extensions whose theme just became active
 		for (const [extensionId, extension] of this.pendingExtensions) {
-			const isActive = this.stylesheetsByExtension.has(extensionId);
-			const shouldBeActive = this.isExtensionThemeActive(extensionId);
-
-			if (shouldBeActive && !isActive) {
+			if (!this.stylesheetsByExtension.has(extensionId) && this.isExtensionThemeActive(extensionId)) {
 				this.activateExtensionCSS(extension);
-			} else if (!shouldBeActive && isActive) {
+			}
+		}
+
+		// Deactivate all extensions whose theme is no longer active,
+		// including cached CSS that may not yet be in pendingExtensions
+		for (const extensionId of this.stylesheetsByExtension.keys()) {
+			if (!this.isExtensionThemeActive(extensionId)) {
 				this.removeStylesheets(extensionId);
 				this.clearCacheForExtension(extensionId);
 			}
diff --git a/test/sanity/src/context.ts b/test/sanity/src/context.ts
index d04fc6703b4a9..62eee018d0687 100644
--- a/test/sanity/src/context.ts
+++ b/test/sanity/src/context.ts
@@ -38,6 +38,7 @@ export class TestContext {
 	private readonly tempDirs = new Set<string>();
 	private readonly wslTempDirs = new Set<string>();
 	private nextPort = 3010;
+	private currentTestName: string | undefined;
 
 	public constructor(public readonly options: Readonly<{
 		quality: 'stable' | 'insider' | 'exploration';
@@ -47,6 +48,7 @@ export class TestContext {
 		checkSigning: boolean;
 		headlessBrowser: boolean;
 		downloadOnly: boolean;
+		screenshotsDir: string | undefined;
 	}>) {
 	}
 
@@ -88,6 +90,7 @@ export class TestContext {
 
 		const self = this;
 		return test(name, async function () {
+			self.currentTestName = name;
 			self.log(`Starting test: ${name}`);
 
 			const homeDir = os.homedir();
@@ -102,6 +105,8 @@ export class TestContext {
 				throw error;
 
 			} finally {
+				self.currentTestName = undefined;
+
 				process.chdir(homeDir);
 				self.log(`Changed working directory to: ${homeDir}`);
 
@@ -1070,6 +1075,26 @@ export class TestContext {
 		return page;
 	}
 
+	/**
+	 * Captures a screenshot of the current page if one is active.
+	 */
+	public async captureScreenshot(page: Page) {
+		if (!this.currentTestName) {
+			return;
+		}
+
+		try {
+			const screenshotDir = this.options.screenshotsDir ?? path.join(this.osTempDir, 'vscode-sanity-screenshots');
+			fs.mkdirSync(screenshotDir, { recursive: true });
+			const sanitizedName = this.currentTestName.replace(/[^a-zA-Z0-9_-]/g, '_');
+			const screenshotPath = path.join(screenshotDir, `${sanitizedName}.png`);
+			await page.screenshot({ path: screenshotPath, fullPage: true });
+			this.log(`Screenshot saved to: ${screenshotPath}`);
+		} catch (e) {
+			this.log(`Failed to capture screenshot: ${e instanceof Error ? e.message : String(e)}`);
+		}
+	}
+
 	/**
 	 * Constructs a web server URL with optional token and folder parameters.
 	 * @param port The port number of the web server.
@@ -1165,7 +1190,7 @@ export class TestContext {
 			await new Promise<void>((resolve, reject) => {
 				app.stderr.on('data', (data) => {
 					const text = `[${name}] ${data.toString().trim()}`;
-					if (/ECONNRESET/.test(text)) {
+					if (/ECONNRESET|ECONNABORTED/.test(text)) {
 						this.log(text);
 					} else {
 						reject(new Error(text));
diff --git a/test/sanity/src/desktop.test.ts b/test/sanity/src/desktop.test.ts
index abb37db72f009..c2d65c157db1c 100644
--- a/test/sanity/src/desktop.test.ts
+++ b/test/sanity/src/desktop.test.ts
@@ -249,12 +249,13 @@ export function setup(context: TestContext) {
 
 		context.log(`Starting VS Code ${entryPoint} with args ${args.join(' ')}`);
 		const app = await _electron.launch({ executablePath: entryPoint, args });
-		const window = await context.getPage(app.firstWindow());
-
-		await test.run(window);
-
-		context.log('Closing the application');
-		await app.close();
+		try {
+			const window = await context.getPage(app.firstWindow());
+			await test.run(window);
+		} finally {
+			context.log('Closing the application');
+			await app.close();
+		}
 
 		test.validate();
 	}
diff --git a/test/sanity/src/index.ts b/test/sanity/src/index.ts
index 6439018a9b601..a251128892529 100644
--- a/test/sanity/src/index.ts
+++ b/test/sanity/src/index.ts
@@ -10,9 +10,9 @@ import path from 'path';
 import { fileURLToPath } from 'url';
 
 const options = minimist(process.argv.slice(2), {
-	string: ['fgrep', 'grep', 'test-results', 'timeout'],
+	string: ['fgrep', 'grep', 'test-results', 'timeout', 'screenshots-dir'],
 	boolean: ['help'],
-	alias: { fgrep: 'f', grep: 'g', help: 'h', 'test-results': 't' },
+	alias: { fgrep: 'f', grep: 'g', help: 'h', 'test-results': 't', 'screenshots-dir': 's' },
 });
 
 if (options.help) {
@@ -28,6 +28,7 @@ if (options.help) {
 	console.info('  --fgrep, -f <string>            Only run tests containing the given <string>');
 	console.info('  --test-results, -t <path>       Output test results in JUnit format to the specified path');
 	console.info('  --timeout <sec>                 Set the test-case timeout in seconds (default: 600 seconds)');
+	console.info('  --screenshots-dir, -s <path>    Save failure screenshots to the specified directory');
 	console.info('  --verbose, -v                   Enable verbose logging');
 	console.info('  --help, -h                      Show this help message');
 	process.exit(0);
diff --git a/test/sanity/src/main.ts b/test/sanity/src/main.ts
index cf3a7780350af..840364e68a52a 100644
--- a/test/sanity/src/main.ts
+++ b/test/sanity/src/main.ts
@@ -13,7 +13,7 @@ import { setup as setupServerWebTests } from './serverWeb.test.js';
 import { setup as setupWSLTests } from './wsl.test.js';
 
 const options = minimist(process.argv.slice(2), {
-	string: ['commit', 'quality'],
+	string: ['commit', 'quality', 'screenshots-dir'],
 	boolean: ['cleanup', 'verbose', 'signing-check', 'headless', 'detection'],
 	alias: { commit: 'c', quality: 'q', verbose: 'v' },
 	default: { cleanup: true, verbose: false, 'signing-check': true, headless: true, 'detection': true },
@@ -35,6 +35,7 @@ const context = new TestContext({
 	checkSigning: options['signing-check'],
 	headlessBrowser: options.headless,
 	downloadOnly: !options['detection'],
+	screenshotsDir: options['screenshots-dir'],
 });
 
 context.log(`Arguments: ${process.argv.slice(2).join(' ')}`);
diff --git a/test/sanity/src/serverWeb.test.ts b/test/sanity/src/serverWeb.test.ts
index 4b765c0cd1083..3099ba70d5a6d 100644
--- a/test/sanity/src/serverWeb.test.ts
+++ b/test/sanity/src/serverWeb.test.ts
@@ -91,18 +91,20 @@ export function setup(context: TestContext) {
 
 				const url = context.getWebServerUrl(port, token, test.workspaceDir).toString();
 				const browser = await context.launchBrowser();
-				const page = await context.getPage(browser.newPage());
+				try {
+					const page = await context.getPage(browser.newPage());
 
-				context.log(`Navigating to ${url}`);
-				await page.goto(url, { waitUntil: 'networkidle' });
+					context.log(`Navigating to ${url}`);
+					await page.goto(url, { waitUntil: 'networkidle' });
 
-				context.log('Waiting for the workbench to load');
-				await page.waitForSelector('.monaco-workbench');
+					context.log('Waiting for the workbench to load');
+					await page.waitForSelector('.monaco-workbench');
 
-				await test.run(page);
-
-				context.log('Closing browser');
-				await browser.close();
+					await test.run(page);
+				} finally {
+					context.log('Closing browser');
+					await browser.close();
+				}
 
 				test.validate();
 				return true;
diff --git a/test/sanity/src/uiTest.ts b/test/sanity/src/uiTest.ts
index f6dda6bc1a4a2..582c4eeab3b4b 100644
--- a/test/sanity/src/uiTest.ts
+++ b/test/sanity/src/uiTest.ts
@@ -52,9 +52,14 @@ export class UITest {
 	 * Run the UI test actions.
 	 */
 	public async run(page: Page) {
-		await this.dismissWorkspaceTrustDialog(page);
-		await this.createTextFile(page);
-		await this.installExtension(page);
+		try {
+			await this.dismissWorkspaceTrustDialog(page);
+			await this.createTextFile(page);
+			await this.installExtension(page);
+		} catch (error) {
+			await this.context.captureScreenshot(page);
+			throw error;
+		}
 	}
 
 	/**
@@ -80,9 +85,11 @@ export class UITest {
 	private async runCommand(page: Page, command: string) {
 		this.context.log(`Running command: ${command}`);
 		await page.keyboard.press('F1');
-		await page.getByPlaceholder(/^Type the name of a command/).fill(`>${command}`);
-		await page.locator('span.monaco-highlighted-label', { hasText: new RegExp(`^${command}$`) }).click();
-		await page.waitForTimeout(1000);
+		const input = page.getByPlaceholder(/^Type the name of a command/);
+		await input.fill(`>${command}`);
+		const item = page.locator('span.monaco-highlighted-label', { hasText: new RegExp(`^${command}$`) });
+		await item.click();
+		await input.waitFor({ state: 'hidden' });
 	}
 
 	/**
@@ -125,15 +132,37 @@ export class UITest {
 
 		this.context.log('Typing extension name to search for');
 		await page.getByText('Search Extensions in Marketplace').focus();
-		await page.keyboard.insertText('GitHub Pull Requests');
+		await page.keyboard.type('GitHub Pull Requests', { delay: 50 });
+
+		this.context.log('Waiting for extension to appear in search results');
+		const extensionItem = page.locator('.extension-list-item').getByText(/^GitHub Pull Requests$/);
+		const messageContainer = page.locator('.extensions-viewlet .message-container:not(.hidden)').first();
+
+		for (let attempt = 0; attempt < 3; attempt++) {
+			const result = await Promise.race([
+				extensionItem.waitFor().then(() => 'found' as const),
+				messageContainer.waitFor().then(() => 'message' as const),
+			]);
+
+			if (result === 'found') {
+				break;
+			}
+
+			const message = await messageContainer.locator('.message').innerText();
+			this.context.log(`Marketplace message: ${message} (attempt ${attempt + 1}/3), clicking Refresh`);
+			await page.getByRole('button', { name: 'Refresh' }).click();
+			await messageContainer.waitFor({ state: 'hidden', timeout: 30_000 });
+		}
+
+		await extensionItem.waitFor();
 
 		this.context.log('Clicking Install on the first extension in the list');
-		await page.locator('.extension-list-item').getByText(/^GitHub Pull Requests$/).waitFor();
-		await page.locator('.extension-action:not(.disabled)', { hasText: /Install/ }).first().click();
-		await page.waitForTimeout(1000);
+		const installButton = page.locator('.extension-action:not(.disabled)', { hasText: /Install/ }).first();
+		await installButton.waitFor();
+		await installButton.click();
 
 		this.context.log('Waiting for extension to be installed');
-		await page.locator('.extension-action:not(.disabled)', { hasText: /Uninstall/ }).waitFor();
+		await page.locator('.extension-action:not(.disabled)', { hasText: /Uninstall/ }).waitFor({ timeout: 5 * 60_1000 });
 	}
 
 	/**
diff --git a/test/sanity/src/wsl.test.ts b/test/sanity/src/wsl.test.ts
index ab2c581763460..77df84d72758f 100644
--- a/test/sanity/src/wsl.test.ts
+++ b/test/sanity/src/wsl.test.ts
@@ -117,18 +117,20 @@ export function setup(context: TestContext) {
 
 				const url = context.getWebServerUrl(port, token, wslWorkspaceDir).toString();
 				const browser = await context.launchBrowser();
-				const page = await context.getPage(browser.newPage());
+				try {
+					const page = await context.getPage(browser.newPage());
 
-				context.log(`Navigating to ${url}`);
-				await page.goto(url, { waitUntil: 'networkidle' });
+					context.log(`Navigating to ${url}`);
+					await page.goto(url, { waitUntil: 'networkidle' });
 
-				context.log('Waiting for the workbench to load');
-				await page.waitForSelector('.monaco-workbench');
+					context.log('Waiting for the workbench to load');
+					await page.waitForSelector('.monaco-workbench');
 
-				await test.run(page);
-
-				context.log('Closing browser');
-				await browser.close();
+					await test.run(page);
+				} finally {
+					context.log('Closing browser');
+					await browser.close();
+				}
 
 				test.validate();
 				return true;
@@ -152,18 +154,20 @@ export function setup(context: TestContext) {
 
 		context.log(`Starting VS Code ${entryPoint} with args ${args.join(' ')}`);
 		const app = await _electron.launch({ executablePath: entryPoint, args });
-		const window = await context.getPage(app.firstWindow());
+		try {
+			const window = await context.getPage(app.firstWindow());
 
-		context.log('Installing WSL extension');
-		await window.getByRole('button', { name: 'Install and Reload' }).click();
+			context.log('Installing WSL extension');
+			await window.getByRole('button', { name: 'Install and Reload' }).click();
 
-		context.log('Waiting for WSL connection');
-		await window.getByText(/WSL/).waitFor();
+			context.log('Waiting for WSL connection');
+			await window.getByText(/WSL/).waitFor();
 
-		await test.run(window);
-
-		context.log('Closing the application');
-		await app.close();
+			await test.run(window);
+		} finally {
+			context.log('Closing the application');
+			await app.close();
+		}
 
 		test.validate();
 	}