diff --git a/services/search/cache.py b/services/search/cache.py
index 222682c7b..a3134abf0 100644
--- a/services/search/cache.py
+++ b/services/search/cache.py
@@ -40,24 +40,37 @@ def generate_cache_key(data: str) -> str:
 def cleanup_cache(cache_dir: Path, cache_index: Dict[str, datetime], max_age: timedelta):
     """Remove expired cache entries and enforce LRU policy."""
     current_time = datetime.now()
-    files_in_dir = {f.name.split(".")[0]: f for f in cache_dir.glob("*.cache")}
+    files_in_dir = {f.stem: f for f in cache_dir.glob("*.cache")}
 
-    to_remove = []
-    for key, timestamp in list(cache_index.items()):
-        if current_time - timestamp > max_age or key not in files_in_dir:
-            to_remove.append(key)
-            if key in files_in_dir:
-                files_in_dir[key].unlink(missing_ok=True)
+    live_entries = []
+    for key, cache_file in list(files_in_dir.items()):
+        timestamp = cache_index.get(key)
+        if timestamp is None:
+            try:
+                timestamp = datetime.fromtimestamp(cache_file.stat().st_mtime)
+            except OSError:
+                continue
+        if current_time - timestamp > max_age:
+            try:
+                cache_file.unlink(missing_ok=True)
+                cache_metrics["evictions"] += 1
+                cache_index.pop(key, None)
+            except OSError as e:
+                logger.debug("Failed to remove expired cache file %s: %s", cache_file, e)
+        else:
+            live_entries.append((key, timestamp, cache_file))
 
-    for key in to_remove:
-        cache_index.pop(key, None)
-        cache_metrics["evictions"] += 1
-
-    if len(cache_index) > CACHE_MAX_ENTRIES:
-        sorted_items = sorted(cache_index.items(), key=lambda x: x[1])
-        excess_count = len(cache_index) - CACHE_MAX_ENTRIES
-        for key, _ in sorted_items[:excess_count]:
+    for key in list(cache_index):
+        if key not in files_in_dir:
             cache_index.pop(key, None)
-            cache_file = cache_dir / f"{key}.cache"
-            cache_file.unlink(missing_ok=True)
             cache_metrics["evictions"] += 1
+
+    if len(live_entries) > CACHE_MAX_ENTRIES:
+        excess_count = len(live_entries) - CACHE_MAX_ENTRIES
+        for key, _, cache_file in sorted(live_entries, key=lambda x: x[1])[:excess_count]:
+            try:
+                cache_file.unlink(missing_ok=True)
+                cache_metrics["evictions"] += 1
+                cache_index.pop(key, None)
+            except OSError as e:
+                logger.debug("Failed to remove excess cache file %s: %s", cache_file, e)
diff --git a/tests/test_search_cache_cleanup.py b/tests/test_search_cache_cleanup.py
new file mode 100644
index 000000000..286eb8295
--- /dev/null
+++ b/tests/test_search_cache_cleanup.py
@@ -0,0 +1,69 @@
+import os
+import time
+from datetime import datetime, timedelta
+from pathlib import Path
+
+from services.search import cache as cache_module
+
+
+def _write_cache_file(cache_dir, key, age_seconds):
+    path = cache_dir / f"{key}.cache"
+    path.write_text("{}", encoding="utf-8")
+    mtime = time.time() - age_seconds
+    os.utime(path, (mtime, mtime))
+    return path
+
+
+def test_cleanup_cache_removes_expired_disk_files_missing_from_index(tmp_path):
+    expired = _write_cache_file(tmp_path, "expired", age_seconds=7200)
+
+    cache_module.cleanup_cache(tmp_path, {}, timedelta(hours=1))
+
+    assert not expired.exists()
+
+
+def test_cleanup_cache_keeps_fresh_disk_files_missing_from_index(tmp_path):
+    fresh = _write_cache_file(tmp_path, "fresh", age_seconds=60)
+
+    cache_module.cleanup_cache(tmp_path, {}, timedelta(hours=1))
+
+    assert fresh.exists()
+
+
+def test_cleanup_cache_enforces_max_entries_against_disk_files(tmp_path, monkeypatch):
+    monkeypatch.setattr(cache_module, "CACHE_MAX_ENTRIES", 2)
+    oldest = _write_cache_file(tmp_path, "oldest", age_seconds=30)
+    newer = _write_cache_file(tmp_path, "newer", age_seconds=20)
+    newest = _write_cache_file(tmp_path, "newest", age_seconds=10)
+
+    cache_module.cleanup_cache(tmp_path, {}, timedelta(hours=1))
+
+    assert not oldest.exists()
+    assert newer.exists()
+    assert newest.exists()
+
+
+def test_cleanup_cache_removes_index_entries_for_missing_files(tmp_path):
+    cache_index = {"missing": datetime.now()}
+
+    cache_module.cleanup_cache(tmp_path, cache_index, timedelta(hours=1))
+
+    assert cache_index == {}
+
+
+def test_cleanup_cache_keeps_index_when_delete_fails(tmp_path, monkeypatch):
+    expired = _write_cache_file(tmp_path, "expired", age_seconds=7200)
+    cache_index = {"expired": datetime.fromtimestamp(expired.stat().st_mtime)}
+    original_unlink = Path.unlink
+
+    def fail_expired_unlink(self, missing_ok=False):
+        if self == expired:
+            raise OSError("delete failed")
+        return original_unlink(self, missing_ok=missing_ok)
+
+    monkeypatch.setattr(Path, "unlink", fail_expired_unlink)
+
+    cache_module.cleanup_cache(tmp_path, cache_index, timedelta(hours=1))
+
+    assert expired.exists()
+    assert "expired" in cache_index