fix: resolve message queue race condition during LLM processing

- Move queue check before status mutation logic to prevent race condition
- Add continuous queue monitoring during pWaitFor to catch messages that arrive during processing
- Process queued messages immediately when detected during wait period
- Add comprehensive tests for queue race condition scenarios

Fixes #8536

src/core/task/Task.ts

@@ -799,10 +799,36 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 		// The state is mutable if the message is complete and the task will
 		// block (via the `pWaitFor`).
 		const isBlocking = !(this.askResponse !== undefined || this.lastMessageTs !== askTs)
-		const isMessageQueued = !this.messageQueueService.isEmpty()
-		const isStatusMutable = !partial && isBlocking && !isMessageQueued
 		let statusMutationTimeouts: NodeJS.Timeout[] = []
 
+		// Process any queued messages first
+		let processedQueuedMessage = false
+		if (!partial && isBlocking && !this.messageQueueService.isEmpty()) {
+			console.log("Task#ask will process message queue")
+
+			const message = this.messageQueueService.dequeueMessage()
+
+			if (message) {
+				processedQueuedMessage = true
+				// Check if this is a tool approval ask that needs to be handled
+				if (
+					type === "tool" ||
+					type === "command" ||
+					type === "browser_action_launch" ||
+					type === "use_mcp_server"
+				) {
+					// For tool approvals, we need to approve first, then send the message if there's text/images
+					this.handleWebviewAskResponse("yesButtonClicked", message.text, message.images)
+				} else {
+					// For other ask types (like followup), fulfill the ask directly
+					this.setMessageResponse(message.text, message.images)
+				}
+			}
+		}
+
+		// Only set status mutations if we didn't process a queued message and there are no more queued messages
+		const isStatusMutable = !partial && isBlocking && !processedQueuedMessage && this.messageQueueService.isEmpty()
+
 		if (isStatusMutable) {
 			console.log(`Task#ask will block -> type: ${type}`)
 
@@ -840,30 +866,41 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 					}, 1_000),
 				)
 			}
-		} else if (isMessageQueued) {
-			console.log("Task#ask will process message queue")
-
-			const message = this.messageQueueService.dequeueMessage()
-
-			if (message) {
-				// Check if this is a tool approval ask that needs to be handled
-				if (
-					type === "tool" ||
-					type === "command" ||
-					type === "browser_action_launch" ||
-					type === "use_mcp_server"
-				) {
-					// For tool approvals, we need to approve first, then send the message if there's text/images
-					this.handleWebviewAskResponse("yesButtonClicked", message.text, message.images)
-				} else {
-					// For other ask types (like followup), fulfill the ask directly
-					this.setMessageResponse(message.text, message.images)
-				}
-			}
 		}
 
-		// Wait for askResponse to be set.
-		await pWaitFor(() => this.askResponse !== undefined || this.lastMessageTs !== askTs, { interval: 100 })
+		// Wait for askResponse to be set, but also check for new queued messages periodically
+		await pWaitFor(
+			() => {
+				// If response is ready, we're done
+				if (this.askResponse !== undefined || this.lastMessageTs !== askTs) {
+					return true
+				}
+
+				// Check if new messages were queued while waiting
+				if (!this.messageQueueService.isEmpty()) {
+					console.log("Task#ask detected new queued message while waiting")
+					const message = this.messageQueueService.dequeueMessage()
+
+					if (message) {
+						// Process the newly queued message
+						if (
+							type === "tool" ||
+							type === "command" ||
+							type === "browser_action_launch" ||
+							type === "use_mcp_server"
+						) {
+							this.handleWebviewAskResponse("yesButtonClicked", message.text, message.images)
+						} else {
+							this.setMessageResponse(message.text, message.images)
+						}
+						return true
+					}
+				}
+
+				return false
+			},
+			{ interval: 100 },
+		)
 
 		if (this.lastMessageTs !== askTs) {
 			// Could happen if we send multiple asks in a row i.e. with

src/core/task/__tests__/Task.spec.ts

@@ -1776,4 +1776,130 @@ describe("Cline", () => {
 			consoleErrorSpy.mockRestore()
 		})
 	})
+
+	describe("Message Queue Race Condition Fix", () => {
+		it("should process messages from queue when available", async () => {
+			const task = new Task({
+				provider: mockProvider,
+				apiConfiguration: mockApiConfig,
+				task: "test task",
+				startTask: false,
+			})
+
+			// Add a message to the queue
+			task.messageQueueService.addMessage("queued message", ["image.png"])
+
+			// Call ask which should process the queued message
+			const result = await task.ask("followup", "Initial question")
+
+			// Verify the queued message was processed
+			expect(result.response).toBe("messageResponse")
+			expect(result.text).toBe("queued message")
+			expect(result.images).toEqual(["image.png"])
+
+			// Verify queue is now empty
+			expect(task.messageQueueService.isEmpty()).toBe(true)
+		})
+
+		it("should handle tool approval messages from queue", async () => {
+			const task = new Task({
+				provider: mockProvider,
+				apiConfiguration: mockApiConfig,
+				task: "test task",
+				startTask: false,
+			})
+
+			// Add a message to the queue
+			task.messageQueueService.addMessage("approve with context", ["image.png"])
+
+			// Call ask for tool approval - should auto-approve with queued message
+			const result = await task.ask("tool", "Do you want to use this tool?")
+
+			// Verify the queued message was processed as tool approval
+			expect(result.response).toBe("yesButtonClicked")
+			expect(result.text).toBe("approve with context")
+			expect(result.images).toEqual(["image.png"])
+
+			// Verify queue is now empty
+			expect(task.messageQueueService.isEmpty()).toBe(true)
+		})
+
+		it("should check for new messages during wait period", async () => {
+			const task = new Task({
+				provider: mockProvider,
+				apiConfiguration: mockApiConfig,
+				task: "test task",
+				startTask: false,
+			})
+
+			// Mock pWaitFor to simulate adding a message during the wait
+			const originalPWaitFor = (await import("p-wait-for")).default
+			let conditionCheckCount = 0
+			vi.mocked(originalPWaitFor).mockImplementation(async (condition, options) => {
+				// Simulate checking the condition multiple times
+				while (true) {
+					conditionCheckCount++
+
+					// On the second check, add a message to the queue
+					if (conditionCheckCount === 2) {
+						task.messageQueueService.addMessage("delayed message")
+						// The condition should now detect the message and process it
+						task.setMessageResponse("delayed message")
+					}
+
+					// Check the condition
+					const result = await condition()
+					if (result) {
+						return
+					}
+
+					// Prevent infinite loop
+					if (conditionCheckCount > 5) {
+						// Force completion
+						task.setMessageResponse("forced completion")
+						return
+					}
+
+					await new Promise((resolve) => setTimeout(resolve, 10))
+				}
+			})
+
+			// Call ask - initially no messages in queue
+			const result = await task.ask("followup", "Question")
+
+			// Should have processed the message that was added during wait
+			expect(result.response).toBe("messageResponse")
+			expect(result.text).toBe("delayed message")
+
+			// Verify condition was checked multiple times
+			expect(conditionCheckCount).toBeGreaterThan(1)
+		})
+
+		it("should handle multiple messages in queue", async () => {
+			const task = new Task({
+				provider: mockProvider,
+				apiConfiguration: mockApiConfig,
+				task: "test task",
+				startTask: false,
+			})
+
+			// Add multiple messages to the queue
+			task.messageQueueService.addMessage("first message")
+			task.messageQueueService.addMessage("second message")
+
+			// First ask should process first message
+			const result1 = await task.ask("followup", "Question 1")
+			expect(result1.text).toBe("first message")
+
+			// Queue should still have one message
+			expect(task.messageQueueService.isEmpty()).toBe(false)
+
+			// Second ask should process second message
+			const result2 = await task.ask("followup", "Question 2")
+			expect(result2.text).toBe("second message")
+
+			// Queue should now be empty
+			expect(task.messageQueueService.isEmpty()).toBe(true)
+		})
+	})
 })