Fix Windows system-path detection and make CLI help assertions robust

src/aci/core/path_utils.py

@@ -93,9 +93,12 @@ def _is_windows_system_directory(resolved: Path, path_str: str) -> bool:
     windows_path = PureWindowsPath(path_str)
     win_parts = [part.lower() for part in windows_path.parts if part not in ("\\", "/")]
 
-    # Strip drive prefix (e.g., "c:") if present.
-    if win_parts and re.fullmatch(r"[a-z]:", win_parts[0]):
-        win_parts = win_parts[1:]
+    # Strip Windows drive/root prefixes (e.g., "c:\\" -> "c:") so the
+    # first semantic directory component can be matched reliably.
+    if win_parts:
+        drive = win_parts[0].rstrip("\\/")
+        if re.fullmatch(r"[a-z]:", drive):
+            win_parts = win_parts[1:]
 
     if win_parts and win_parts[0] in WINDOWS_SYSTEM_DIRS:
         return True

tests/unit/test_cli.py

@@ -4,13 +4,20 @@
 Tests the basic functionality of CLI commands and error handling.
 """
 
+import re
+
 from typer.testing import CliRunner
 
 from aci.cli import app
 
 runner = CliRunner()
 
 
+def _plain(text: str) -> str:
+    """Remove ANSI escape sequences for stable assertions."""
+    return re.sub(r"\x1b\[[0-9;]*m", "", text)
+
+
 class TestCLIHelp:
     """Test CLI help and usage information."""
 
@@ -29,17 +36,20 @@ def test_index_help(self):
         result = runner.invoke(app, ["index", "--help"])
 
         assert result.exit_code == 0
-        assert "Directory to index" in result.stdout
-        assert "--workers" in result.stdout
+        output = _plain(result.stdout)
+        assert "Directory to index" in output
+        assert "workers" in output
+        assert "-w" in output
 
     def test_search_help(self):
         """Search command help should display options."""
         result = runner.invoke(app, ["search", "--help"])
 
         assert result.exit_code == 0
-        assert "Search query" in result.stdout
-        assert "--limit" in result.stdout
-        assert "--filter" in result.stdout
+        output = _plain(result.stdout)
+        assert "Search query" in output
+        assert "limit" in output
+        assert "filter" in output
 
     def test_update_help(self):
         """Update command help should display options."""