diff --git a/backend/open_webui/utils/context_compaction.py b/backend/open_webui/utils/context_compaction.py
index d3955148cb..c70c7785b7 100644
--- a/backend/open_webui/utils/context_compaction.py
+++ b/backend/open_webui/utils/context_compaction.py
@@ -305,8 +305,13 @@ def _build_context_usage(tokens: int, threshold: int) -> dict:
 def _apply_latest_summary_checkpoint(messages: list[dict]) -> tuple[list[dict], str | None]:
     summary = None
     summary_idx = None
+    cut_idx = None
+    kept_output = None
 
     for idx, message in enumerate(messages):
+        if checkpoint := _find_tool_loop_checkpoint(messages, idx):
+            summary, cut_idx, kept_output = checkpoint
+            summary_idx = cut_idx - 1
         value = message.get('contextSummary') or message.get('context_summary')
         if isinstance(value, str) and value.strip():
             summary = value
@@ -314,7 +319,36 @@ def _apply_latest_summary_checkpoint(messages: list[dict]) -> tuple[list[dict],
 
     if summary_idx is None:
         return messages, None
-    return messages[summary_idx:], summary
+    return [
+        {**message, 'output': kept_output} if idx == cut_idx else message
+        for idx, message in enumerate(messages)
+        if idx >= summary_idx
+    ], summary
+
+
+def _find_tool_loop_checkpoint(messages: list[dict], idx: int) -> tuple[str, int, list[dict]] | None:
+    """Tool loop summary saved in this reply, with the reply it cut and that reply's remaining output."""
+    output = messages[idx].get('output') or []
+    marker = next((item for item in reversed(output) if item.get('type') == 'open_webui:context_compaction'), None)
+    if not marker:
+        return None
+    # The loop can cut into an earlier reply when this one started near the threshold.
+    for cut_idx in range(idx, -1, -1):
+        cut_output = messages[cut_idx].get('output') or []
+        start = next(
+            (
+                position
+                for position, item in enumerate(cut_output)
+                if item.get('type') == 'function_call' and item.get('call_id') == marker['call_id']
+            ),
+            None,
+        )
+        if start is not None:
+            while start and cut_output[start - 1].get('type') != 'function_call_output':
+                start -= 1
+            kept_output = [item for item in cut_output[start:] if item.get('type') != 'open_webui:context_compaction']
+            return marker['summary'], cut_idx, kept_output
+    return None
 
 
 def _exceeds_token_threshold(messages: list[dict], system_prompt: str, summary: str | None, threshold: int) -> bool:
diff --git a/backend/open_webui/utils/middleware.py b/backend/open_webui/utils/middleware.py
index 1adfba67fd..76b1e8950d 100644
--- a/backend/open_webui/utils/middleware.py
+++ b/backend/open_webui/utils/middleware.py
@@ -6326,6 +6326,20 @@ async def streaming_chat_response_handler(response, ctx):
                                         idx for idx, message in enumerate(messages) if message.get('role') != 'system'
                                     )
                                     messages[checkpoint] = {**messages[checkpoint], 'contextSummary': context_summary}
+                                    kept_call_id = next(
+                                        message['tool_calls'][0]['id']
+                                        for message in messages
+                                        if message.get('tool_calls')
+                                    )
+                                    output.append(
+                                        {
+                                            'type': 'open_webui:context_compaction',
+                                            'id': output_id('cc'),
+                                            'call_id': kept_call_id,
+                                            'summary': context_summary,
+                                        }
+                                    )
+                                    await emit_output()
                             except Exception:
                                 log.exception('Tool loop context compaction failed; keeping the current context')