diff --git a/src/cli/App.tsx b/src/cli/App.tsx
index 00fb22a..1edae82 100644
--- a/src/cli/App.tsx
+++ b/src/cli/App.tsx
@@ -369,7 +369,7 @@ export default function App({
   // Message queue state for queueing messages during streaming
   const [messageQueue, setMessageQueue] = useState<string[]>([]);
 
-  // Queue cancellation: when queue length > 1, we send cancel and wait for natural stream end
+  // Queue cancellation: when any message is queued, we send cancel and wait for stream to end
   const waitingForQueueCancelRef = useRef(false);
   const queueSnapshotRef = useRef<string[]>([]);
   const [restoreQueueOnCancel, setRestoreQueueOnCancel] = useState(false);
@@ -736,6 +736,57 @@ export default function App({
               return;
             }
 
+            // If in quietCancel mode (user queued messages), auto-reject all approvals
+            // and send denials + queued messages together
+            if (waitingForQueueCancelRef.current) {
+              if (restoreQueueOnCancelRef.current) {
+                // User hit ESC during queue cancel - abort the auto-send
+                setRestoreQueueOnCancel(false);
+                // Don't clear queue, don't send - let dequeue effect handle them one by one
+              } else {
+                // Create denial results for all approvals
+                const denialResults = approvalsToProcess.map(
+                  (approvalItem) => ({
+                    type: "approval" as const,
+                    tool_call_id: approvalItem.toolCallId,
+                    approve: false,
+                    reason: "User cancelled - new message queued",
+                  }),
+                );
+
+                // Update buffers to show tools as cancelled
+                for (const approvalItem of approvalsToProcess) {
+                  onChunk(buffersRef.current, {
+                    message_type: "tool_return_message",
+                    id: "dummy",
+                    date: new Date().toISOString(),
+                    tool_call_id: approvalItem.toolCallId,
+                    tool_return: "Cancelled - user sent new message",
+                    status: "error",
+                  });
+                }
+                refreshDerived();
+
+                // Queue denial results to be sent with the queued message
+                setQueuedApprovalResults(denialResults);
+
+                // Get queued messages and clear queue
+                const concatenatedMessage = queueSnapshotRef.current.join("\n");
+                setMessageQueue([]);
+
+                // Send via onSubmit which will combine queuedApprovalResults + message
+                if (concatenatedMessage.trim()) {
+                  onSubmitRef.current(concatenatedMessage);
+                }
+              }
+
+              // Reset flags
+              waitingForQueueCancelRef.current = false;
+              queueSnapshotRef.current = [];
+              setStreaming(false);
+              return;
+            }
+
             // Check permissions for all approvals (including fancy UI tools)
             const approvalResults = await Promise.all(
               approvalsToProcess.map(async (approvalItem) => {
@@ -863,10 +914,6 @@ export default function App({
                 return;
               }
 
-              // Rotate to a new thinking message
-              setThinkingMessage(getRandomThinkingMessage());
-              refreshDerived();
-
               // Combine auto-allowed results + auto-denied responses
               const allResults = [
                 ...autoAllowedResults.map((ar) => ({
@@ -885,6 +932,37 @@ export default function App({
                 })),
               ];
 
+              // Check if user queued messages during auto-allowed tool execution
+              if (waitingForQueueCancelRef.current) {
+                if (restoreQueueOnCancelRef.current) {
+                  // User hit ESC during queue cancel - abort the auto-send
+                  setRestoreQueueOnCancel(false);
+                } else {
+                  // Queue results to be sent with the queued message
+                  setQueuedApprovalResults(allResults);
+
+                  // Get queued messages and clear queue
+                  const concatenatedMessage =
+                    queueSnapshotRef.current.join("\n");
+                  setMessageQueue([]);
+
+                  // Send via onSubmit
+                  if (concatenatedMessage.trim()) {
+                    onSubmitRef.current(concatenatedMessage);
+                  }
+                }
+
+                // Reset flags
+                waitingForQueueCancelRef.current = false;
+                queueSnapshotRef.current = [];
+                setStreaming(false);
+                return;
+              }
+
+              // Rotate to a new thinking message
+              setThinkingMessage(getRandomThinkingMessage());
+              refreshDerived();
+
               await processConversation([
                 {
                   type: "approval",
@@ -894,6 +972,68 @@ export default function App({
               return;
             }
 
+            // Check again if user queued messages during auto-allowed tool execution
+            if (waitingForQueueCancelRef.current) {
+              if (restoreQueueOnCancelRef.current) {
+                // User hit ESC during queue cancel - abort the auto-send
+                setRestoreQueueOnCancel(false);
+              } else {
+                // Create denial results for tools that need user input
+                const denialResults = needsUserInput.map((ac) => ({
+                  type: "approval" as const,
+                  tool_call_id: ac.approval.toolCallId,
+                  approve: false,
+                  reason: "User cancelled - new message queued",
+                }));
+
+                // Update buffers to show tools as cancelled
+                for (const ac of needsUserInput) {
+                  onChunk(buffersRef.current, {
+                    message_type: "tool_return_message",
+                    id: "dummy",
+                    date: new Date().toISOString(),
+                    tool_call_id: ac.approval.toolCallId,
+                    tool_return: "Cancelled - user sent new message",
+                    status: "error",
+                  });
+                }
+                refreshDerived();
+
+                // Combine with auto-handled results and queue for sending
+                const allResults = [
+                  ...autoAllowedResults.map((ar) => ({
+                    type: "tool" as const,
+                    tool_call_id: ar.toolCallId,
+                    tool_return: ar.result.toolReturn,
+                    status: ar.result.status,
+                  })),
+                  ...autoDeniedResults.map((ad) => ({
+                    type: "approval" as const,
+                    tool_call_id: ad.approval.toolCallId,
+                    approve: false,
+                    reason: ad.reason,
+                  })),
+                  ...denialResults,
+                ];
+                setQueuedApprovalResults(allResults);
+
+                // Get queued messages and clear queue
+                const concatenatedMessage = queueSnapshotRef.current.join("\n");
+                setMessageQueue([]);
+
+                // Send via onSubmit
+                if (concatenatedMessage.trim()) {
+                  onSubmitRef.current(concatenatedMessage);
+                }
+              }
+
+              // Reset flags
+              waitingForQueueCancelRef.current = false;
+              queueSnapshotRef.current = [];
+              setStreaming(false);
+              return;
+            }
+
             // Show approval dialog for tools that need user input
             setPendingApprovals(needsUserInput.map((ac) => ac.approval));
             setApprovalContexts(
@@ -1102,11 +1242,11 @@ export default function App({
         setMessageQueue((prev) => {
           const newQueue = [...prev, msg];
 
-          // If queue grows to 2+ messages and we're not already waiting for cancel,
-          // send cancel request and capture snapshot
-          if (newQueue.length > 1 && !waitingForQueueCancelRef.current) {
-            // Capture snapshot of queue right now
-            queueSnapshotRef.current = [...newQueue];
+          // Always update snapshot to include ALL queued messages
+          queueSnapshotRef.current = [...newQueue];
+
+          // If this is the first queued message, send cancel request
+          if (!waitingForQueueCancelRef.current) {
             waitingForQueueCancelRef.current = true;
 
             // Send cancel request to backend (fire-and-forget)