diff --git a/src/@types/vscode.proposed.chatContextProvider.d.ts b/src/@types/vscode.proposed.chatContextProvider.d.ts
index a3b20144fa..ee971b9adb 100644
--- a/src/@types/vscode.proposed.chatContextProvider.d.ts
+++ b/src/@types/vscode.proposed.chatContextProvider.d.ts
@@ -39,6 +39,10 @@ declare module 'vscode' {
 		 * An optional description of the context item, e.g. to describe the item to the language model.
 		 */
 		modelDescription?: string;
+		/**
+		 * An optional tooltip to show when hovering over the context item in the UI.
+		 */
+		tooltip?: MarkdownString;
 		/**
 		 * The value of the context item. Can be omitted when returned from one of the `provide` methods if the provider supports `resolveChatContext`.
 		 */
diff --git a/src/extension.ts b/src/extension.ts
index f99a2b30ff..a65dfd4232 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -269,9 +269,9 @@ async function init(
 	context.subscriptions.push(issuesFeatures);
 	await issuesFeatures.initialize();
 
-	const pullRequestContextProvider = new PullRequestContextProvider(prsTreeModel, reposManager, git);
+	const pullRequestContextProvider = new PullRequestContextProvider(prsTreeModel, reposManager, git, context);
 	vscode.chat.registerChatContextProvider({ scheme: 'webview-panel', pattern: '**/webview-PullRequestOverview**' }, 'githubpr', pullRequestContextProvider);
-	vscode.chat.registerChatContextProvider({ scheme: 'webview-panel', pattern: '**/webview-IssueOverview**' }, 'githubissue', new IssueContextProvider(issueStateManager, reposManager));
+	vscode.chat.registerChatContextProvider({ scheme: 'webview-panel', pattern: '**/webview-IssueOverview**' }, 'githubissue', new IssueContextProvider(issueStateManager, reposManager, context));
 	pullRequestContextProvider.initialize();
 
 	const notificationsFeatures = new NotificationsFeatureRegister(credentialStore, reposManager, telemetry, notificationsManager);
diff --git a/src/lm/issueContextProvider.ts b/src/lm/issueContextProvider.ts
index 79a9689c54..83a36c5067 100644
--- a/src/lm/issueContextProvider.ts
+++ b/src/lm/issueContextProvider.ts
@@ -7,6 +7,7 @@ import * as vscode from 'vscode';
 import { CommentEvent, EventType } from '../common/timelineEvent';
 import { IssueModel } from '../github/issueModel';
 import { IssueOverviewPanel } from '../github/issueOverview';
+import { issueMarkdown } from '../github/markdownUtils';
 import { RepositoriesManager } from '../github/repositoriesManager';
 import { getIssueNumberLabel } from '../github/utils';
 import { IssueQueryResult, StateManager } from '../issues/stateManager';
@@ -23,7 +24,8 @@ export namespace IssueChatContextItem {
 
 export class IssueContextProvider implements vscode.ChatContextProvider {
 	constructor(private readonly _stateManager: StateManager,
-		private readonly _reposManager: RepositoriesManager
+		private readonly _reposManager: RepositoriesManager,
+		private readonly _context: vscode.ExtensionContext
 	) { }
 
 	async provideChatContextForResource(_options: { resource: vscode.Uri }, _token: vscode.CancellationToken): Promise<IssueChatContextItem | undefined> {
@@ -36,6 +38,7 @@ export class IssueContextProvider implements vscode.ChatContextProvider {
 	async resolveChatContext(context: IssueChatContextItem, _token: vscode.CancellationToken): Promise<vscode.ChatContextItem> {
 		context.value = await this._resolvedIssueValue(context.issue);
 		context.modelDescription = 'All the information about the GitHub issue the user is viewing, including comments.';
+		context.tooltip = await issueMarkdown(context.issue, this._context, this._reposManager);
 		return context;
 	}
 
@@ -71,6 +74,7 @@ export class IssueContextProvider implements vscode.ChatContextProvider {
 			icon: new vscode.ThemeIcon('issues'),
 			label: `#${issue.number} ${issue.title}`,
 			modelDescription: 'The GitHub issue the user is viewing.',
+			tooltip: new vscode.MarkdownString(`#${issue.number} ${issue.title}`),
 			issue,
 			command: {
 				command: 'issue.openDescription',
diff --git a/src/lm/pullRequestContextProvider.ts b/src/lm/pullRequestContextProvider.ts
index d311bf6611..f8963f5229 100644
--- a/src/lm/pullRequestContextProvider.ts
+++ b/src/lm/pullRequestContextProvider.ts
@@ -7,6 +7,7 @@ import * as vscode from 'vscode';
 import { GitApiImpl } from '../api/api1';
 import { Disposable } from '../common/lifecycle';
 import { onceEvent } from '../common/utils';
+import { issueMarkdown } from '../github/markdownUtils';
 import { PullRequestModel } from '../github/pullRequestModel';
 import { PullRequestOverviewPanel } from '../github/pullRequestOverview';
 import { RepositoriesManager } from '../github/repositoriesManager';
@@ -28,7 +29,8 @@ export class PullRequestContextProvider extends Disposable implements vscode.Cha
 
 	constructor(private readonly _prsTreeModel: PrsTreeModel,
 		private readonly _reposManager: RepositoriesManager,
-		private readonly _git: GitApiImpl
+		private readonly _git: GitApiImpl,
+		private readonly _context: vscode.ExtensionContext
 	) {
 		super();
 	}
@@ -102,6 +104,7 @@ Active pull request (may not be the same as open pull request): ${folderManager.
 		}
 		context.value = await this._resolvedPrValue(context.pr);
 		context.modelDescription = 'All the information about the GitHub pull request the user is viewing, including comments, review threads, and changes.';
+		context.tooltip = await issueMarkdown(context.pr, this._context, this._reposManager);
 		return context;
 	}
 
@@ -117,6 +120,7 @@ Active pull request (may not be the same as open pull request): ${folderManager.
 			icon: new vscode.ThemeIcon('git-pull-request'),
 			label: `#${pr.number} ${pr.title}`,
 			modelDescription: 'The GitHub pull request the user is viewing.',
+			tooltip: new vscode.MarkdownString(`#${pr.number} ${pr.title}`),
 			pr,
 			command: {
 				command: 'pr.openDescription',