diff --git a/src/cli/App.tsx b/src/cli/App.tsx
index 2582153..331a9c9 100644
--- a/src/cli/App.tsx
+++ b/src/cli/App.tsx
@@ -6423,12 +6423,45 @@ DO NOT respond to these messages or otherwise consider them in your response unl
     if (approval?.toolName === "ExitPlanMode") {
       // First check if plan mode is enabled
       if (permissionMode.getMode() !== "plan") {
-        handlePlanKeepPlanning(
-          `Plan mode is not currently enabled. Use EnterPlanMode to enter plan mode first, then write your plan and use ExitPlanMode to present it.`,
-        );
+        // Plan mode state was lost (e.g., CLI restart) - queue rejection with helpful message
+        // This is different from immediate rejection because we want the user to see what happened
+        // and be able to type their next message
+
+        // Add status message to explain what happened
+        const statusId = uid("status");
+        buffersRef.current.byId.set(statusId, {
+          kind: "status",
+          id: statusId,
+          lines: ["⚠️ Plan mode session expired (use /plan to re-enter)"],
+        });
+        buffersRef.current.order.push(statusId);
+
+        // Queue denial to send with next message (same pattern as handleCancelApprovals)
+        const denialResults = [
+          {
+            type: "approval" as const,
+            tool_call_id: approval.toolCallId,
+            approve: false,
+            reason:
+              "Plan mode session expired (CLI restarted). Use EnterPlanMode to re-enter plan mode, or request the user to re-enter plan mode.",
+          },
+        ];
+        setQueuedApprovalResults(denialResults);
+
+        // Mark tool as cancelled in buffers
+        markIncompleteToolsAsCancelled(buffersRef.current);
+        refreshDerived();
+
+        // Clear all approval state (same as handleCancelApprovals)
+        setPendingApprovals([]);
+        setApprovalContexts([]);
+        setApprovalResults([]);
+        setAutoHandledResults([]);
+        setAutoDeniedApprovals([]);
         return;
       }
-      // Then check if plan file exists
+      // Then check if plan file exists (keep existing behavior - immediate rejection)
+      // This case means plan mode IS active, but agent forgot to write the plan file
       if (!planFileExists()) {
         const planFilePath = permissionMode.getPlanFilePath();
         const plansDir = join(homedir(), ".letta", "plans");
@@ -6439,7 +6472,12 @@ DO NOT respond to these messages or otherwise consider them in your response unl
         );
       }
     }
-  }, [pendingApprovals, approvalResults.length, handlePlanKeepPlanning]);
+  }, [
+    pendingApprovals,
+    approvalResults.length,
+    handlePlanKeepPlanning,
+    refreshDerived,
+  ]);
 
   const handleQuestionSubmit = useCallback(
     async (answers: Record<string, string>) => {
@@ -7024,6 +7062,7 @@ Plan file path: ${planFilePath}`;
                               handlePlanApprove(true)
                             }
                             onKeepPlanning={handlePlanKeepPlanning}
+                            onCancel={handleCancelApprovals}
                             isFocused={true}
                           />
                         ) : isFileEditApproval && fileEditInfo ? (
diff --git a/src/cli/components/StaticPlanApproval.tsx b/src/cli/components/StaticPlanApproval.tsx
index 2e05791..5806116 100644
--- a/src/cli/components/StaticPlanApproval.tsx
+++ b/src/cli/components/StaticPlanApproval.tsx
@@ -9,6 +9,7 @@ type Props = {
   onApprove: () => void;
   onApproveAndAcceptEdits: () => void;
   onKeepPlanning: (reason: string) => void;
+  onCancel: () => void; // For CTRL-C to queue denial (like other approval screens)
   isFocused?: boolean;
 };
 
@@ -28,6 +29,7 @@ export const StaticPlanApproval = memo(
     onApprove,
     onApproveAndAcceptEdits,
     onKeepPlanning,
+    onCancel,
     isFocused = true,
   }: Props) => {
     const [selectedOption, setSelectedOption] = useState(0);
@@ -50,9 +52,9 @@ export const StaticPlanApproval = memo(
       (input, key) => {
         if (!isFocused) return;
 
-        // CTRL-C: keep planning with cancel message
+        // CTRL-C: cancel and queue denial (like other approval screens)
         if (key.ctrl && input === "c") {
-          onKeepPlanning("User pressed CTRL-C to cancel");
+          onCancel();
           return;
         }