diff --git a/nanobot/agent/loop.py b/nanobot/agent/loop.py
index b5fe774c..001009bb 100644
--- a/nanobot/agent/loop.py
+++ b/nanobot/agent/loop.py
@@ -2063,7 +2063,12 @@ class AgentLoop:
             try:
                 session = self.sessions.get_or_create(key)
                 changed = False
-                had_pending = False
+                # Capture pending flag before _restore_runtime_checkpoint
+                # clears it (it clears both checkpoint and pending_turn at
+                # lines 1966-1967).
+                had_pending = bool(
+                    session.metadata.get(self._PENDING_USER_TURN_KEY)
+                )
                 if self._restore_runtime_checkpoint(session):
                     changed = True
                 if self._restore_pending_user_turn(session):