diff --git a/nanobot/agent/loop.py b/nanobot/agent/loop.py
index eba037c4b..949e21116 100644
--- a/nanobot/agent/loop.py
+++ b/nanobot/agent/loop.py
@@ -1592,13 +1592,13 @@ class AgentLoop:
                 continue  # skip empty assistant messages — they poison session context
             if role == "tool":
                 tool_call_id = entry.get("tool_call_id")
-                if tool_call_id and str(tool_call_id) not in declared_tool_call_ids:
+                if not tool_call_id or str(tool_call_id) not in declared_tool_call_ids:
                     # A tool result without a declared call violates the
                     # OpenAI/Anthropic pairing contract and would poison
                     # every future request built from this session (#4006).
                     logger.warning(
                         "Dropping orphaned tool result {} from session {} during persistence",
-                        tool_call_id,
+                        tool_call_id or "(missing id)",
                         session.key,
                     )
                     continue
diff --git a/tests/agent/test_loop_save_turn.py b/tests/agent/test_loop_save_turn.py
index 20ea99694..fc0f49f5d 100644
--- a/tests/agent/test_loop_save_turn.py
+++ b/tests/agent/test_loop_save_turn.py
@@ -1406,6 +1406,23 @@ def test_save_turn_drops_orphaned_tool_results() -> None:
     assert [m["role"] for m in session.messages] == ["user", "assistant"]
 
 
+def test_save_turn_drops_tool_results_without_tool_call_id() -> None:
+    loop = _mk_loop()
+    session = Session(key="test:missing-tool-call-id")
+    session.add_message("user", "hi")
+
+    loop._save_turn(
+        session,
+        [
+            {"role": "tool", "name": "exec", "content": "missing id"},
+            {"role": "assistant", "content": "done"},
+        ],
+        skip=0,
+    )
+
+    assert [m["role"] for m in session.messages] == ["user", "assistant"]
+
+
 def test_save_turn_keeps_tool_results_declared_in_prior_history() -> None:
     # Declarations may live in already-persisted history (e.g. a restored
     # runtime checkpoint), not only in the new-turn slice.