diff --git a/backend/app/service/chat_service.py b/backend/app/service/chat_service.py
index 5e17be91e..56c1fe704 100644
--- a/backend/app/service/chat_service.py
+++ b/backend/app/service/chat_service.py
@@ -428,6 +428,8 @@ async def step_solve(options: Chat, request: Request, task_lock: TaskLock):
 
                 # Check if this might be a misrouted second question
                 if camel_task is None and workforce is None:
+                    logger.error(f"Cannot add task: both camel_task and workforce are None for project {options.project_id}")
+                    yield sse_json("error", {"message": "Cannot add task: task not initialized. Please start a task first."})
                     continue
 
                 assert camel_task is not None
diff --git a/src/components/ChatBox/index.tsx b/src/components/ChatBox/index.tsx
index e2321fac5..fd9f6fd11 100644
--- a/src/components/ChatBox/index.tsx
+++ b/src/components/ChatBox/index.tsx
@@ -168,9 +168,6 @@ export default function ChatBox(): JSX.Element {
 					chatStore.setAttaches(_taskId, []); // Clear attaches after queuing
 					setMessage("");
 					if (textareaRef.current) textareaRef.current.style.height = "60px";
-					toast.success("Task queued. It will be processed when the current task finishes.", {
-						closeButton: true,
-					});
 
 					//Send the task as soon as possible
 					//Workforce internal queue handles it
@@ -185,9 +182,17 @@ export default function ChatBox(): JSX.Element {
 								timestamp: Date.now()
 							}
 						});
+
+						// Only show success toast after API call succeeds
+						toast.success("Task queued. It will be processed when the current task finishes.", {
+							closeButton: true,
+						});
 					} catch (error) {
 						console.error(`Removing Message "${tempMessageContent}..." due to ${error}`)
 						projectStore.removeQueuedMessage(project_id as string, new_task_id);
+						toast.error("Failed to queue task. Please try again.", {
+							closeButton: true,
+						});
 					}
 					return;
 				}
@@ -591,14 +596,21 @@ export default function ChatBox(): JSX.Element {
 			//Optimistic Removal
 			projectStore.removeQueuedMessage(project_id, task_id);
 
-			//Call api only when workforce has been run at least once
-			//Note: Replay creates a new chatstore, so no conflicts
+			// Always try to call the backend to remove the task
+			// The backend will handle the error gracefully if workforce is not initialized
+			// Note: Replay creates a new chatstore, so no conflicts
 			const task = chatStore.tasks[chatStore.activeTaskId as string];
-			if(task.messages && task.messages.some(m => m.step === 'to_sub_tasks') && task.status === "running") {
-				await fetchDelete(`/chat/${project_id}/remove-task/${task_id}`, {
-					project_id: project_id,
-					task_id: task_id
-				});
+			// Only skip backend call if task is finished or hasn't started yet (no messages)
+			if(task && task.messages.length > 0 && task.status !== 'finished') {
+				try {
+					await fetchDelete(`/chat/${project_id}/remove-task/${task_id}`, {
+						project_id: project_id,
+						task_id: task_id
+					});
+				} catch (apiError) {
+					// If backend returns an error, it's okay - the task might not be in the workforce queue yet
+					console.log(`Backend remove call failed (expected if workforce not started): ${apiError}`);
+				}
 			}
 		} catch (error) {
 			// Revert the optimistic removal by restoring the original message