diff --git a/agent/context_compressor.py b/agent/context_compressor.py
index a51a65d11bbd..082420920d1e 100644
--- a/agent/context_compressor.py
+++ b/agent/context_compressor.py
@@ -2777,6 +2777,15 @@ def compress(self, messages: List[Dict[str, Any]], current_tokens: int = None, f
             if summary_body and not self._previous_summary:
                 self._previous_summary = summary_body
             turns_to_summarize = messages[max(compress_start, summary_idx + 1):compress_end]
+            if not turns_to_summarize:
+                self._ineffective_compression_count += 1
+                self._last_compression_savings_pct = 0.0
+                if not self.quiet_mode:
+                    logger.warning(
+                        "Compression skipped: latest context summary leaves no messages "
+                        "between protected head and tail"
+                    )
+                return messages
         elif self._previous_summary:
             # No handoff summary found in the current messages, but
             # _previous_summary is non-empty — it was set by a different