diff --git a/CLAUDE.md b/CLAUDE.md
index bf7405a..cc30da5 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -53,6 +53,13 @@ You are the Runewager Bot Ops Commander. You manage the full lifecycle of the Ru
 - Health monitoring after deployment
 - Proactive improvements
 
+## Runewager 2.0 Agent Contract (Map-First)
+- Treat `RUNEWAGER_FUNCTIONALITY_MAP.md` as the operational source of truth before and after every change.
+- Implement functionality in code first, then immediately sync map/docs to match real behavior.
+- Never ship doc-only behavior claims that are not implemented and tested.
+- Before marking any task done: run tests/smoke checks, verify command↔callback↔menu reachability, and confirm pending-state recovery paths.
+- Any added/removed flow must be reflected in `RUNEWAGER_FUNCTIONALITY_MAP.md` in the same change set.
+
 ## Workflow Patterns
 1. git pull origin main
 2. Install dependencies as needed (npm install / pip install -r requirements.txt)
diff --git a/RUNEWAGER_FUNCTIONALITY_MAP.md b/RUNEWAGER_FUNCTIONALITY_MAP.md
index 2995f2b..8688467 100644
--- a/RUNEWAGER_FUNCTIONALITY_MAP.md
+++ b/RUNEWAGER_FUNCTIONALITY_MAP.md
@@ -208,7 +208,7 @@ Configured/observed time behaviors:
 - Periodic persistence intervals and scheduler timers (content drops, maintenance timers).
 - Giveaway timers drive auto finalization and countdown behavior.
 
-No universal pendingAction timeout/auto-cancel was detected for all user/admin input flows.
+Pending-action timeout handling is enforced in the text input router: each pending state receives/retains `createdAt`, expires after 15 minutes, clears state, and returns a Main Menu recovery panel. Command escapes (`/cancel`, `/menu`, `/start`, `/help`) also clear pending states safely.
 
 ## 17. Validation Rules (username, discord, etc.)
 
diff --git a/index.js b/index.js
index d4b7685..fd70aeb 100644
--- a/index.js
+++ b/index.js
@@ -380,6 +380,30 @@ const NON_USERNAME_WORDS = new Set([
 // Slash commands implemented in this file. Used for unknown-command fallback.
 const PENDING_ACTION_TIMEOUT_MS = 15 * 60 * 1000; // 15m timeout for wait-for-input states
 
+/**
+ * Evaluate and normalize a user's pendingAction timeout metadata.
+ *
+ * Returns an object with:
+ * - hadPending: whether a pending action existed
+ * - expired: whether it was cleared due to timeout
+ * - expiredType: pending action type cleared (if expired)
+ */
+function evaluatePendingActionTimeout(user, now = Date.now()) {
+  if (!user || !user.pendingAction) {
+    return { hadPending: false, expired: false, expiredType: null };
+  }
+
+  if (!user.pendingAction.createdAt) user.pendingAction.createdAt = now;
+
+  if ((now - Number(user.pendingAction.createdAt || 0)) <= PENDING_ACTION_TIMEOUT_MS) {
+    return { hadPending: true, expired: false, expiredType: null };
+  }
+
+  const expiredType = user.pendingAction.type || 'current action';
+  user.pendingAction = null;
+  return { hadPending: true, expired: true, expiredType };
+}
+
 const REGISTERED_COMMANDS = new Set([
   'A',
   'a',
@@ -9187,13 +9211,10 @@ bot.on('text', async (ctx) => {
 
   const text = (ctx.message.text || '').trim();
 
-  if (user.pendingAction && !user.pendingAction.createdAt) user.pendingAction.createdAt = Date.now();
-
-  if (user.pendingAction && (Date.now() - Number(user.pendingAction.createdAt || 0)) > PENDING_ACTION_TIMEOUT_MS) {
-    const expiredType = user.pendingAction.type || 'current action';
-    user.pendingAction = null;
+  const pendingTimeoutState = evaluatePendingActionTimeout(user);
+  if (pendingTimeoutState.expired) {
     await ctx.reply(
-      `⏱️ Your pending step (${expiredType}) timed out after 15 minutes. Please start again from the menu.`,
+      `⏱️ Your pending step (${pendingTimeoutState.expiredType}) timed out after 15 minutes. Please start again from the menu.`,
       Markup.inlineKeyboard([[Markup.button.callback('🏠 Main Menu', 'to_main_menu')], [Markup.button.callback('❌ Cancel', 'to_main_menu')]]),
     );
     return;
diff --git a/test/unit.test.js b/test/unit.test.js
index 51e5c9c..8e6183c 100644
--- a/test/unit.test.js
+++ b/test/unit.test.js
@@ -174,6 +174,23 @@ function getNextOnboardingStep(user) {
   return 5;
 }
 
+
+function evaluatePendingActionTimeout(user, now = Date.now()) {
+  if (!user || !user.pendingAction) {
+    return { hadPending: false, expired: false, expiredType: null };
+  }
+
+  if (!user.pendingAction.createdAt) user.pendingAction.createdAt = now;
+
+  if ((now - Number(user.pendingAction.createdAt || 0)) <= 15 * 60 * 1000) {
+    return { hadPending: true, expired: false, expiredType: null };
+  }
+
+  const expiredType = user.pendingAction.type || 'current action';
+  user.pendingAction = null;
+  return { hadPending: true, expired: true, expiredType };
+}
+
 // ---------------------------------------------------------------------------
 // Bonus status state machine
 // ---------------------------------------------------------------------------
@@ -328,6 +345,34 @@ test('onboarding step 5 (done) when all steps complete', () => {
   assert.equal(getNextOnboardingStep(user), 5);
 });
 
+
+
+test('pending action timeout seeds createdAt on first check', () => {
+  const now = 1700000000000;
+  const user = { pendingAction: { type: 'await_tip_add_text' } };
+  const out = evaluatePendingActionTimeout(user, now);
+  assert.equal(out.expired, false);
+  assert.equal(out.hadPending, true);
+  assert.equal(user.pendingAction.createdAt, now);
+});
+
+test('pending action timeout expires after 15 minutes and clears state', () => {
+  const now = 1700000900001;
+  const user = { pendingAction: { type: 'await_tip_add_text', createdAt: now - (15 * 60 * 1000) - 1 } };
+  const out = evaluatePendingActionTimeout(user, now);
+  assert.equal(out.expired, true);
+  assert.equal(out.expiredType, 'await_tip_add_text');
+  assert.equal(user.pendingAction, null);
+});
+
+test('pending action timeout uses fallback type label when missing', () => {
+  const now = 1700000900001;
+  const user = { pendingAction: { createdAt: now - (15 * 60 * 1000) - 1 } };
+  const out = evaluatePendingActionTimeout(user, now);
+  assert.equal(out.expired, true);
+  assert.equal(out.expiredType, 'current action');
+});
+
 // ---------------------------------------------------------------------------
 // Promo claim limit check (pure logic)
 // ---------------------------------------------------------------------------