diff --git a/gateway/session.py b/gateway/session.py
index 7a1273e93..605a3602f 100644
--- a/gateway/session.py
+++ b/gateway/session.py
@@ -1193,12 +1193,14 @@ class SessionStore:
                 # end_reason not None -> session ended — prune
                 if row is not None and row.get("end_reason") is not None:
                     recovered_entry = None
+                    recovery_lookup_failed = False
                     if entry.origin is not None:
                         try:
                             recovered_entry = self._recover_session_from_db(
                                 session_key=key,
                                 source=entry.origin,
                                 now=_now(),
+                                raise_on_lookup_error=True,
                             )
                         except Exception as exc:
                             logger.debug(
@@ -1208,6 +1210,10 @@ class SessionStore:
                                 entry.session_id,
                                 exc,
                             )
+                            recovery_lookup_failed = True
+
+                    if recovery_lookup_failed:
+                        continue
 
                     # If the stale entry points at a compression-ended parent but
                     # a newer live child session exists for the exact same gateway
@@ -1431,6 +1437,7 @@ class SessionStore:
         session_key: str,
         source: SessionSource,
         now: datetime,
+        raise_on_lookup_error: bool = False,
     ) -> Optional[SessionEntry]:
         """Rebuild a missing session-key mapping from durable state.db data."""
         if not self._db:
@@ -1449,6 +1456,8 @@ class SessionStore:
             )
         except Exception as exc:
             logger.debug("Gateway session DB recovery failed for %s: %s", session_key, exc)
+            if raise_on_lookup_error:
+                raise
             return None
         if not recovered:
             return None
diff --git a/tests/gateway/test_session_store_stale_prune.py b/tests/gateway/test_session_store_stale_prune.py
index 9b8cf1fe4..c5811adad 100644
--- a/tests/gateway/test_session_store_stale_prune.py
+++ b/tests/gateway/test_session_store_stale_prune.py
@@ -151,6 +151,25 @@ class TestPruneStaleSessionsLocked:
 
         assert key not in store._entries
 
+    def test_keeps_stale_entry_when_recovery_lookup_raises(self, tmp_path):
+        """Indeterminate recovery must not delete the only routing handle.
+
+        Startup pruning sees an ended parent and tries to repoint it to the
+        latest live gateway child.  If that recovery query raises, deleting the
+        sessions.json entry loses the routing key entirely; keeping it lets the
+        runtime stale guard retry recovery on the next message.
+        """
+        key = "agent:main:telegram:dm:5140768830"
+        db = _db_returning({"sid_parent": {"end_reason": "compression", "id": "sid_parent"}})
+        db.find_latest_gateway_session_for_peer.side_effect = RuntimeError("db busy")
+        store = _make_store_with_db(tmp_path, db)
+        store._entries[key] = _make_entry_with_origin(key, "sid_parent")
+
+        store._prune_stale_sessions_locked()
+
+        assert key in store._entries
+        assert store._entries[key].session_id == "sid_parent"
+
     def test_noop_when_db_is_none(self, tmp_path):
         config = GatewayConfig(default_reset_policy=SessionResetPolicy(mode="none"))
         with patch("gateway.session.SessionStore._ensure_loaded"):