diff --git a/src/context_compactor.py b/src/context_compactor.py
index c87ea4c43..b92c7d752 100644
--- a/src/context_compactor.py
+++ b/src/context_compactor.py
@@ -381,7 +381,10 @@ async def maybe_compact(
         )
     except Exception as e:
         logger.error(f"Compaction summary failed: {e}")
-        return system_msgs + recent, context_length, False
+        # Degrade gracefully: keep the conversation intact rather than
+        # silently dropping the older half. was_compacted=False signals the
+        # caller nothing was summarized; trim_for_context handles length.
+        return messages, context_length, False
 
     summary_msg = {
         "role": "system",
diff --git a/tests/test_compaction_summary_failure.py b/tests/test_compaction_summary_failure.py
new file mode 100644
index 000000000..f69f7e58d
--- /dev/null
+++ b/tests/test_compaction_summary_failure.py
@@ -0,0 +1,97 @@
+"""Regression test for #2160: when the compaction summary LLM call fails,
+maybe_compact must return the original messages unchanged, not the older half
+dropped. Uses mock imports to avoid loading the full app stack."""
+
+import asyncio
+import sys
+from unittest.mock import MagicMock
+
+import pytest
+
+# Mock heavy dependencies before importing
+for mod in [
+    'sqlalchemy', 'sqlalchemy.orm', 'sqlalchemy.ext', 'sqlalchemy.ext.declarative',
+    'sqlalchemy.ext.hybrid', 'sqlalchemy.sql', 'sqlalchemy.sql.expression',
+    'src.database',
+    'core.models', 'core.database',
+]:
+    if mod not in sys.modules:
+        sys.modules[mod] = MagicMock()
+
+import src.context_compactor as cc
+from src.context_compactor import maybe_compact
+
+
+class TestCompactionSummaryFailure:
+    """When the summary call raises, no conversation history may be lost.
+
+    On success maybe_compact replaces the older half with a summary message.
+    On failure it must degrade gracefully and hand back the original messages
+    list unchanged, so the next turn (or trim_for_context) can handle length.
+    Before the fix the except branch returned `system_msgs + recent`, silently
+    discarding the older half while reporting was_compacted=False — the caller
+    then treated a materially shorter list as a no-op."""
+
+    def _run(self, messages, *, context_length=100):
+        # Force compaction to trigger (pct over COMPACT_THRESHOLD) and make the
+        # summary call fail, so the except branch runs. Stub everything so the
+        # test is hermetic (no network, no real endpoint resolution).
+        orig_ctx = cc.get_context_length
+        orig_est = cc.estimate_tokens
+        orig_call = cc.llm_call_async
+        orig_resolve = cc.resolve_endpoint
+        orig_update = cc._update_session_history
+
+        async def _boom(*a, **k):
+            raise RuntimeError("summary model down")
+
+        cc.get_context_length = lambda url, model: context_length
+        cc.estimate_tokens = lambda msgs: 10000  # well over the threshold
+        cc.llm_call_async = _boom
+        cc.resolve_endpoint = lambda which: (None, None, None)
+        cc._update_session_history = lambda *a, **k: None
+        try:
+            return asyncio.run(
+                maybe_compact(
+                    session=None,
+                    endpoint_url="http://local/v1/chat/completions",
+                    model="local-model",
+                    messages=list(messages),
+                    headers={},
+                )
+            )
+        finally:
+            cc.get_context_length = orig_ctx
+            cc.estimate_tokens = orig_est
+            cc.llm_call_async = orig_call
+            cc.resolve_endpoint = orig_resolve
+            cc._update_session_history = orig_update
+
+    def _history(self):
+        return [
+            {"role": "system", "content": "PRESET"},
+            {"role": "user", "content": "OLDER-1"},
+            {"role": "assistant", "content": "OLDER-2"},
+            {"role": "user", "content": "OLDER-3"},
+            {"role": "assistant", "content": "RECENT-1"},
+            {"role": "user", "content": "RECENT-2"},
+            {"role": "assistant", "content": "RECENT-3"},
+        ]
+
+    def test_returns_original_messages_when_summary_fails(self):
+        messages = self._history()
+        out, _ctx, was_compacted = self._run(messages)
+
+        # Nothing was actually compacted.
+        assert was_compacted is False
+        # The full original list comes back unchanged — including the older half.
+        assert out == messages
+
+    def test_older_messages_not_dropped_on_failure(self):
+        messages = self._history()
+        out, _ctx, _was = self._run(messages)
+
+        contents = [m["content"] for m in out]
+        # The older half must survive the failed summary call.
+        for older in ("OLDER-1", "OLDER-2", "OLDER-3"):
+            assert older in contents