diff --git a/src/cli/App.tsx b/src/cli/App.tsx
index d8276cb..acb1759 100644
--- a/src/cli/App.tsx
+++ b/src/cli/App.tsx
@@ -156,6 +156,12 @@ NOTE: At any point in time through this workflow you should feel free to ask the
 `;
 }
 
+// Check if plan file exists
+function planFileExists(): boolean {
+  const planFilePath = permissionMode.getPlanFilePath();
+  return !!planFilePath && existsSync(planFilePath);
+}
+
 // Read plan content from the plan file
 function readPlanFile(): string {
   const planFilePath = permissionMode.getPlanFilePath();
@@ -825,8 +831,9 @@ export default function App({
             // Check permissions for all approvals (including fancy UI tools)
             const approvalResults = await Promise.all(
               approvalsToProcess.map(async (approvalItem) => {
-                // Check if approval is incomplete (missing name or arguments)
-                if (!approvalItem.toolName || !approvalItem.toolArgs) {
+                // Check if approval is incomplete (missing name)
+                // Note: toolArgs can be empty string for tools with no arguments (e.g., EnterPlanMode)
+                if (!approvalItem.toolName) {
                   return {
                     approval: approvalItem,
                     permission: {
@@ -3251,6 +3258,20 @@ ${recentCommits}
     [pendingApprovals, approvalResults, sendAllResults],
   );
 
+  // Auto-reject ExitPlanMode if plan file doesn't exist
+  useEffect(() => {
+    const currentIndex = approvalResults.length;
+    const approval = pendingApprovals[currentIndex];
+    if (approval?.toolName === "ExitPlanMode" && !planFileExists()) {
+      const planFilePath = permissionMode.getPlanFilePath();
+      handlePlanKeepPlanning(
+        `You must write your plan to the plan file before exiting plan mode.\n` +
+          `Plan file path: ${planFilePath || "not set"}\n` +
+          `Use the Write tool to create your plan, then call ExitPlanMode again.`,
+      );
+    }
+  }, [pendingApprovals, approvalResults.length, handlePlanKeepPlanning]);
+
   const handleQuestionSubmit = useCallback(
     async (answers: Record<string, string>) => {
       const currentIndex = approvalResults.length;
diff --git a/src/cli/components/ToolCallMessageRich.tsx b/src/cli/components/ToolCallMessageRich.tsx
index b0b4ac7..432976b 100644
--- a/src/cli/components/ToolCallMessageRich.tsx
+++ b/src/cli/components/ToolCallMessageRich.tsx
@@ -272,8 +272,9 @@ export const ToolCallMessage = memo(({ line }: { line: ToolCallLine }) => {
 
     // Format tool denial errors more user-friendly
     if (isError && displayText.includes("request to call tool denied")) {
-      const match = displayText.match(/User reason: (.+)$/);
-      const reason = match ? match[1] : "(empty)";
+      // Use [\s\S]+ to match multiline reasons
+      const match = displayText.match(/User reason: ([\s\S]+)$/);
+      const reason = match?.[1]?.trim() || "(empty)";
       displayText = `User rejected the tool call with reason: ${reason}`;
     }
 
diff --git a/src/permissions/mode.ts b/src/permissions/mode.ts
index b37e4ff..0160c00 100644
--- a/src/permissions/mode.ts
+++ b/src/permissions/mode.ts
@@ -124,6 +124,11 @@ class PermissionModeManager {
           "Grep",
           "NotebookRead",
           "TodoWrite",
+          // Plan mode tools (must allow exit!)
+          "ExitPlanMode",
+          "exit_plan_mode",
+          "AskUserQuestion",
+          "ask_user_question",
           // Codex toolset (snake_case)
           "read_file",
           "list_dir",
diff --git a/src/tools/impl/ExitPlanMode.ts b/src/tools/impl/ExitPlanMode.ts
index 5e73259..c6bcaf1 100644
--- a/src/tools/impl/ExitPlanMode.ts
+++ b/src/tools/impl/ExitPlanMode.ts
@@ -6,6 +6,7 @@
 export async function exit_plan_mode(): Promise<{ message: string }> {
   // Return confirmation message that plan was approved
   // Note: The plan is read from the plan file by the UI before this return is shown
+  // The UI layer checks if the plan file exists and auto-rejects if not
   return {
     message:
       "User has approved your plan. You can now start coding.\nStart with updating your todo list if applicable",