diff --git a/agent/conversation_loop.py b/agent/conversation_loop.py
index 1884c06489d9d..db04d95cc8352 100644
--- a/agent/conversation_loop.py
+++ b/agent/conversation_loop.py
@@ -4360,9 +4360,11 @@ def run_conversation(
                     compression_attempts += 1
                     if compression_attempts <= max_compression_attempts:
                         original_len = len(messages)
+                        # Option A (LCM issue 441): overhead-aware request size so recovery arms on
+                        # the true request (msgs + tools + system), not the tool-blind message count.
                         messages, active_system_prompt = agent._compress_context(
                             messages, system_message,
-                            approx_tokens=approx_tokens,
+                            approx_tokens=estimate_request_tokens_rough(api_messages, tools=agent.tools or None),
                             task_id=effective_task_id,
                         )
                         conversation_history = conversation_history_after_compression(
@@ -4617,8 +4619,11 @@ def run_conversation(
                     original_len = len(messages)
                     original_tokens = estimate_messages_tokens_rough(messages)
                     _overflow_input = messages
+                    # Option A (LCM issue 441): overhead-aware request size so recovery arms on the
+                    # true request (msgs + tools + system), not the tool-blind message count.
                     messages, active_system_prompt = agent._compress_context(
-                        messages, system_message, approx_tokens=approx_tokens,
+                        messages, system_message,
+                        approx_tokens=estimate_request_tokens_rough(api_messages, tools=agent.tools or None),
                         task_id=effective_task_id,
                     )
                     if messages is _overflow_input and compression_skipped_due_to_lock(agent):
@@ -4878,8 +4883,13 @@ def run_conversation(
                     original_len = len(messages)
                     original_tokens = estimate_messages_tokens_rough(messages)
                     _overflow_input = messages
+                    # Option A (LCM issue 441): pass the OVERHEAD-AWARE request size (msgs + tool
+                    # schemas + system), not the tool-blind message count, so LCM forced-overflow
+                    # recovery arms on the TRUE request that overflowed. See hermes-lcm engine
+                    # _should_force_overflow_recovery. (approx_tokens stays for the status display.)
                     messages, active_system_prompt = agent._compress_context(
-                        messages, system_message, approx_tokens=approx_tokens,
+                        messages, system_message,
+                        approx_tokens=estimate_request_tokens_rough(api_messages, tools=agent.tools or None),
                         task_id=effective_task_id,
                     )
                     if messages is _overflow_input and compression_skipped_due_to_lock(agent):