fix: improve message queue reliability when AI is working

- Add VS Code notifications for queue success/failure
- Implement error recovery to restore user input when queueing fails
- Enhance error handling with proper user feedback
- Prevent data loss by preserving user messages on queue failures

Fixes #8033

src/core/webview/webviewMessageHandler.ts

@@ -2995,17 +2995,59 @@ export const webviewMessageHandler = async (
 		 */
 
 		case "queueMessage": {
-			provider.getCurrentTask()?.messageQueueService.addMessage(message.text ?? "", message.images)
+			const currentTask = provider.getCurrentTask()
+			if (currentTask && currentTask.messageQueueService) {
+				const queuedMessage = currentTask.messageQueueService.addMessage(message.text ?? "", message.images)
+				if (queuedMessage) {
+					provider.log(`Message queued successfully: ${queuedMessage.id}`)
+					// Send confirmation back to webview
+					provider.postMessageToWebview({
+						type: "messageQueued",
+						success: true,
+						messageId: queuedMessage.id,
+					})
+					// Show VS Code notification for success
+					vscode.window.showInformationMessage("Message queued. It will be sent when the AI is ready.")
+				} else {
+					provider.log(`Failed to queue message: empty text and no images`)
+					provider.postMessageToWebview({
+						type: "messageQueued",
+						success: false,
+						error: "Message cannot be empty",
+						text: message.text,
+						images: message.images,
+					})
+				}
+			} else {
+				provider.log(`Failed to queue message: No active task or message queue service`)
+				provider.postMessageToWebview({
+					type: "messageQueued",
+					success: false,
+					error: "No active task to queue message",
+					text: message.text,
+					images: message.images,
+				})
+				// Show VS Code notification for failure
+				vscode.window.showErrorMessage("Failed to queue message: No active task. Please try again.")
+			}
 			break
 		}
 		case "removeQueuedMessage": {
-			provider.getCurrentTask()?.messageQueueService.removeMessage(message.text ?? "")
+			const currentTask = provider.getCurrentTask()
+			if (currentTask && currentTask.messageQueueService) {
+				const success = currentTask.messageQueueService.removeMessage(message.text ?? "")
+				provider.log(`Message removal ${success ? "successful" : "failed"}: ${message.text}`)
+			}
 			break
 		}
 		case "editQueuedMessage": {
 			if (message.payload) {
 				const { id, text, images } = message.payload as EditQueuedMessagePayload
-				provider.getCurrentTask()?.messageQueueService.updateMessage(id, text, images)
+				const currentTask = provider.getCurrentTask()
+				if (currentTask && currentTask.messageQueueService) {
+					const success = currentTask.messageQueueService.updateMessage(id, text, images)
+					provider.log(`Message edit ${success ? "successful" : "failed"}: ${id}`)
+				}
 			}
 
 			break

src/shared/ExtensionMessage.ts

@@ -124,6 +124,8 @@ export interface ExtensionMessage {
 		| "commands"
 		| "insertTextIntoTextarea"
 		| "dismissedUpsells"
+		| "messageQueued"
+		| "showNotification"
 	text?: string
 	payload?: any // Add a generic payload for now, can refine later
 	action?:
@@ -201,6 +203,9 @@ export interface ExtensionMessage {
 	commands?: Command[]
 	queuedMessages?: QueuedMessage[]
 	list?: string[] // For dismissedUpsells
+	messageId?: string // For messageQueued response
+	level?: "error" | "warning" | "info" // For showNotification
+	message?: string // For showNotification
 }
 
 export type ExtensionState = Pick<

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

@@ -595,15 +595,22 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 
 			if (text || images.length > 0) {
 				if (sendingDisabled) {
+					// Queue the message when sending is disabled
 					try {
 						console.log("queueMessage", text, images)
 						vscode.postMessage({ type: "queueMessage", text, images })
+
+						// Clear the input immediately for better UX
+						// The backend will confirm if queueing was successful
 						setInputValue("")
 						setSelectedImages([])
 					} catch (error) {
 						console.error(
 							`Failed to queue message: ${error instanceof Error ? error.message : String(error)}`,
 						)
+						// Keep the input so user doesn't lose their message
+						// In webview context, we can't show VS Code notifications directly
+						// The error will be logged to console for debugging
 					}
 
 					return
@@ -781,6 +788,30 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 			const message: ExtensionMessage = e.data
 
 			switch (message.type) {
+				case "messageQueued":
+					// Handle message queue confirmation from backend
+					if (!message.success) {
+						// If queueing failed, show error and restore the input
+						console.error("Message queueing failed:", message.error)
+						// Restore the user's input since queueing failed
+						if (message.text || message.images?.length) {
+							setInputValue(message.text || "")
+							setSelectedImages(message.images || [])
+						}
+					} else {
+						console.log("Message queued successfully:", message.messageId)
+					}
+					break
+				case "showNotification":
+					// Handle notification messages from backend
+					if (message.level === "error") {
+						console.error(message.message)
+					} else if (message.level === "warning") {
+						console.warn(message.message)
+					} else {
+						console.log(message.message)
+					}
+					break
 				case "action":
 					switch (message.action!) {
 						case "didBecomeVisible":