diff --git a/codex-lens/src/codexlens/search/chain_search.py b/codex-lens/src/codexlens/search/chain_search.py
index 37b34515..23a20f19 100644
--- a/codex-lens/src/codexlens/search/chain_search.py
+++ b/codex-lens/src/codexlens/search/chain_search.py
@@ -337,12 +337,41 @@ class ChainSearchEngine:
                                 root_cmp = root_str.lower().rstrip("\\/")
                                 dir_cmp = file_dir_str.lower().rstrip("\\/")
 
+                                # Guard against Windows cross-drive comparisons (ValueError).
+                                if os.name == "nt":
+                                    root_drive, _ = os.path.splitdrive(root_cmp)
+                                    dir_drive, _ = os.path.splitdrive(dir_cmp)
+                                    if root_drive and dir_drive and root_drive != dir_drive:
+                                        self.logger.debug(
+                                            "Skipping symbol due to cross-drive path (root=%s file=%s name=%s)",
+                                            root_cmp,
+                                            sym.file,
+                                            sym.name,
+                                        )
+                                        continue
+
                                 if os.path.commonpath([root_cmp, dir_cmp]) != root_cmp:
                                     continue
 
                                 rel = os.path.relpath(dir_cmp, root_cmp)
                                 rel_depth = 0 if rel == "." else len(rel.split(os.sep))
-                            except Exception:
+                            except ValueError as exc:
+                                self.logger.debug(
+                                    "Skipping symbol due to path operation failure (root=%s file=%s name=%s): %s",
+                                    str(search_root),
+                                    sym.file,
+                                    sym.name,
+                                    exc,
+                                )
+                                continue
+                            except Exception as exc:
+                                self.logger.debug(
+                                    "Skipping symbol due to unexpected path error (root=%s file=%s name=%s): %s",
+                                    str(search_root),
+                                    sym.file,
+                                    sym.name,
+                                    exc,
+                                )
                                 continue
 
                             if options.depth >= 0 and rel_depth > options.depth:
diff --git a/codex-lens/tests/test_chain_search.py b/codex-lens/tests/test_chain_search.py
new file mode 100644
index 00000000..d62a859a
--- /dev/null
+++ b/codex-lens/tests/test_chain_search.py
@@ -0,0 +1,81 @@
+import logging
+import os
+import tempfile
+from pathlib import Path
+from unittest.mock import MagicMock
+
+import pytest
+
+from codexlens.config import Config
+from codexlens.entities import Symbol
+from codexlens.search.chain_search import ChainSearchEngine, SearchOptions
+from codexlens.storage.global_index import GlobalSymbolIndex
+from codexlens.storage.path_mapper import PathMapper
+from codexlens.storage.registry import RegistryStore
+
+
+@pytest.fixture()
+def temp_paths():
+    tmpdir = tempfile.TemporaryDirectory(ignore_cleanup_errors=True)
+    root = Path(tmpdir.name)
+    yield root
+    try:
+        tmpdir.cleanup()
+    except (PermissionError, OSError):
+        pass
+
+
+def test_symbol_filtering_handles_path_failures(monkeypatch: pytest.MonkeyPatch, caplog, temp_paths: Path) -> None:
+    project_root = temp_paths / "project"
+    (project_root / "src").mkdir(parents=True, exist_ok=True)
+
+    index_root = temp_paths / "indexes"
+    mapper = PathMapper(index_root=index_root)
+    index_db_path = mapper.source_to_index_db(project_root)
+    index_db_path.parent.mkdir(parents=True, exist_ok=True)
+    index_db_path.write_text("", encoding="utf-8")  # existence is enough for _find_start_index
+
+    registry = RegistryStore(db_path=temp_paths / "registry.db")
+    registry.initialize()
+    project_info = registry.register_project(project_root, mapper.source_to_index_dir(project_root))
+
+    global_db_path = project_info.index_root / GlobalSymbolIndex.DEFAULT_DB_NAME
+    global_index = GlobalSymbolIndex(global_db_path, project_id=project_info.id)
+    global_index.initialize()
+
+    valid_file = project_root / "src" / "auth.py"
+    valid_sym = Symbol(name="AuthManager", kind="class", range=(1, 2), file=str(valid_file))
+    bad_null = Symbol(name="BadNull", kind="class", range=(1, 2), file="bad\0path.py")
+    bad_relative = Symbol(name="BadRelative", kind="class", range=(1, 2), file="relative/path.py")
+
+    candidates = [valid_sym, bad_null, bad_relative]
+
+    if os.name == "nt":
+        root_drive, _ = os.path.splitdrive(str(project_root.resolve()))
+        other_drive = "C:" if root_drive.lower() != "c:" else "D:"
+        candidates.append(
+            Symbol(name="CrossDrive", kind="class", range=(1, 2), file=f"{other_drive}\\other\\file.py")
+        )
+
+    def fake_search(self, name: str, kind=None, limit: int = 20, prefix_mode: bool = False):
+        return candidates
+
+    monkeypatch.setattr(GlobalSymbolIndex, "search", fake_search)
+
+    config = Config(data_dir=temp_paths / "data", global_symbol_index_enabled=True)
+    engine = ChainSearchEngine(registry, mapper, config=config)
+    engine._search_symbols_parallel = MagicMock(side_effect=AssertionError("should not traverse chain"))
+
+    caplog.set_level(logging.DEBUG, logger="codexlens.search.chain_search")
+    symbols = engine.search_symbols(
+        "Auth",
+        project_root,
+        options=SearchOptions(depth=5, total_limit=10),
+    )
+
+    assert [s.name for s in symbols] == ["AuthManager"]
+    assert "BadNull" in caplog.text
+    assert "BadRelative" in caplog.text
+    if os.name == "nt":
+        assert "CrossDrive" in caplog.text
+