fix: handle checkpoint initialization failure gracefully for nested git repos

- Properly reset checkpointServiceInitializing flag when init fails
- Allow task to continue without checkpoints when nested git repos detected
- Show user-friendly warning message instead of blocking task
- Update checkpoint warning display logic to handle cancelled tasks
- Ensure task messages are preserved even when checkpoint init fails

Fixes #7765

Author: roomote

src/core/checkpoints/index.ts

@@ -168,6 +168,17 @@ async function checkGitInstallation(
 		} catch (err) {
 			log(`[Task#getCheckpointService] initShadowGit -> ${err.message}`)
 			task.enableCheckpoints = false
+			task.checkpointServiceInitializing = false
+
+			// If the error is due to nested git repositories, show a user-friendly message
+			// but don't prevent the task from continuing
+			if (err.message?.includes("nested git repositories")) {
+				await vscode.window.showWarningMessage(
+					"Checkpoints are disabled because nested git repositories were detected in the workspace. The task will continue without checkpoint support.",
+					"OK",
+				)
+				// Task can continue without checkpoints
+			}
 		}
 	} catch (err) {
 		log(`[Task#getCheckpointService] Unexpected error during Git check: ${err.message}`)

src/core/task/Task.ts

@@ -1661,7 +1661,11 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 
 	private async initiateTaskLoop(userContent: Anthropic.Messages.ContentBlockParam[]): Promise<void> {
 		// Kicks off the checkpoints initialization process in the background.
-		getCheckpointService(this)
+		// Don't await this - let it run in the background so task can continue even if it fails
+		getCheckpointService(this).catch((error) => {
+			console.log(`[Task#initiateTaskLoop] Checkpoint service initialization failed: ${error.message}`)
+			// Task continues without checkpoints
+		})
 
 		let nextUserContent = userContent
 		let includeFileDetails = true

webview-ui/src/components/chat/ChatView.tsx

@@ -1412,9 +1412,13 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 	// Effect to handle showing the checkpoint warning after a delay
 	useEffect(() => {
 		// Only show the warning when there's a task but no visible messages yet
+		// AND the task is not abandoned (which happens when user cancels)
 		if (task && modifiedMessages.length === 0 && !isStreaming && !isHidden) {
 			const timer = setTimeout(() => {
-				setShowCheckpointWarning(true)
+				// Check if the task still exists and hasn't been abandoned before showing warning
+				if (task && modifiedMessages.length === 0) {
+					setShowCheckpointWarning(true)
+				}
 			}, 5000) // 5 seconds
 
 			return () => clearTimeout(timer)
@@ -1423,12 +1427,12 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 		}
 	}, [task, modifiedMessages.length, isStreaming, isHidden])
 
-	// Effect to hide the checkpoint warning when messages appear
+	// Effect to hide the checkpoint warning when messages appear or task changes
 	useEffect(() => {
-		if (modifiedMessages.length > 0 || isStreaming || isHidden) {
+		if (modifiedMessages.length > 0 || isStreaming || isHidden || !task) {
 			setShowCheckpointWarning(false)
 		}
-	}, [modifiedMessages.length, isStreaming, isHidden])
+	}, [modifiedMessages.length, isStreaming, isHidden, task])
 
 	const placeholderText = task ? t("chat:typeMessage") : t("chat:typeTask")