From df91823800a86b3a7c4efcd613cc857c28f8476d Mon Sep 17 00:00:00 2001
From: arkon <arkon.85@hotmail.com>
Date: Wed, 21 Jan 2026 05:34:45 +0100
Subject: [PATCH] fix: improve memory safety and regex pattern handling

- Add withTimeout utility for async operation protection
- Move Promise callback cleanup earlier in stop() to prevent orphaned refs
- Fix regex lastIndex resets in inner-loop-tracker (reset BEFORE test)
- Add DEFAULT_ASYNC_TIMEOUT_MS and INTERACTIVE_START_TIMEOUT_MS constants

Co-Authored-By: Claude Opus 4.5 <noreply@anthropic.com>
---
 src/inner-loop-tracker.ts |  8 +++----
 src/session.ts            | 48 ++++++++++++++++++++++++++++++++++-----
 2 files changed, 46 insertions(+), 10 deletions(-)

diff --git a/src/inner-loop-tracker.ts b/src/inner-loop-tracker.ts
index 3744e68b..99003f58 100644
--- a/src/inner-loop-tracker.ts
+++ b/src/inner-loop-tracker.ts
@@ -461,21 +461,21 @@ export class InnerLoopTracker extends EventEmitter {
     }
 
     // Todo checkboxes: "- [ ] Task" or "- [x] Task"
+    // Reset lastIndex BEFORE test to ensure consistent matching with /g flag patterns
+    TODO_CHECKBOX_PATTERN.lastIndex = 0;
     if (TODO_CHECKBOX_PATTERN.test(data)) {
-      // Reset lastIndex since we're reusing the global regex
-      TODO_CHECKBOX_PATTERN.lastIndex = 0;
       return true;
     }
 
     // Todo indicator icons: "Todo: ☐", "Todo: ◐", etc.
+    TODO_INDICATOR_PATTERN.lastIndex = 0;
     if (TODO_INDICATOR_PATTERN.test(data)) {
-      TODO_INDICATOR_PATTERN.lastIndex = 0;
       return true;
     }
 
     // Claude Code native todo format: "☐ Task", "☒ Task"
+    TODO_NATIVE_PATTERN.lastIndex = 0;
     if (TODO_NATIVE_PATTERN.test(data)) {
-      TODO_NATIVE_PATTERN.lastIndex = 0;
       return true;
     }
 
diff --git a/src/session.ts b/src/session.ts
index 8fd69402..ee20374a 100644
--- a/src/session.ts
+++ b/src/session.ts
@@ -26,6 +26,7 @@ import { ScreenManager } from './screen-manager.js';
 
 export type { BackgroundTask } from './task-tracker.js';
 export type { InnerLoopState, InnerTodoItem } from './types.js';
+export { withTimeout };
 
 // ============================================================================
 // Buffer Size Constants
@@ -52,6 +53,12 @@ const MAX_LINE_BUFFER_SIZE = 64 * 1024;
 /** Line buffer flush interval (100ms) - forces processing of partial lines */
 const LINE_BUFFER_FLUSH_INTERVAL = 100;
 
+/** Default timeout for async operations in milliseconds (5 minutes) */
+const DEFAULT_ASYNC_TIMEOUT_MS = 5 * 60 * 1000;
+
+/** Timeout for interactive session startup in milliseconds (30 seconds) */
+const INTERACTIVE_START_TIMEOUT_MS = 30 * 1000;
+
 // Filter out terminal focus escape sequences (focus in/out reports)
 // ^[[I (focus in), ^[[O (focus out), and the enable/disable sequences
 const FOCUS_ESCAPE_FILTER = /\x1b\[\?1004[hl]|\x1b\[[IO]/g;
@@ -131,6 +138,33 @@ class BufferAccumulator {
   }
 }
 
+/**
+ * Wraps a promise with a timeout to prevent indefinite hangs.
+ * If the promise doesn't resolve within the timeout, rejects with TimeoutError.
+ *
+ * @param promise - The promise to wrap
+ * @param timeoutMs - Timeout in milliseconds
+ * @param operation - Description of the operation for error messages
+ * @returns Promise that resolves/rejects with the original result or timeout error
+ */
+function withTimeout<T>(
+  promise: Promise<T>,
+  timeoutMs: number,
+  operation: string
+): Promise<T> {
+  let timeoutId: NodeJS.Timeout;
+
+  const timeoutPromise = new Promise<never>((_, reject) => {
+    timeoutId = setTimeout(() => {
+      reject(new Error(`${operation} timed out after ${timeoutMs}ms`));
+    }, timeoutMs);
+  });
+
+  return Promise.race([promise, timeoutPromise]).finally(() => {
+    clearTimeout(timeoutId);
+  });
+}
+
 /**
  * Represents a JSON message from Claude CLI's stream-json output format.
  * Messages are newline-delimited JSON objects parsed from PTY output.
@@ -1253,6 +1287,14 @@ export class Session extends EventEmitter {
       this._lineBufferFlushTimer = null;
     }
 
+    // Immediately cleanup Promise callbacks to prevent orphaned references
+    // during the rest of stop() processing (e.g., if screen kill times out)
+    if (this.rejectPromise) {
+      this.rejectPromise(new Error('Session stopped'));
+    }
+    this.resolvePromise = null;
+    this.rejectPromise = null;
+
     if (this.ptyProcess) {
       const pid = this.ptyProcess.pid;
 
@@ -1306,12 +1348,6 @@ export class Session extends EventEmitter {
       console.log('[Session] Keeping screen session alive:', this._screenSession.screenName);
       this._screenSession = null; // Detach but don't kill
     }
-
-    if (this.rejectPromise) {
-      this.rejectPromise(new Error('Session stopped'));
-      this.resolvePromise = null;
-      this.rejectPromise = null;
-    }
   }
 
   assignTask(taskId: string): void {