diff --git a/src/debugpy/_vendored/pydevd/pydevd_file_utils.py b/src/debugpy/_vendored/pydevd/pydevd_file_utils.py
index fe6d5fd46..caff70f17 100644
--- a/src/debugpy/_vendored/pydevd/pydevd_file_utils.py
+++ b/src/debugpy/_vendored/pydevd/pydevd_file_utils.py
@@ -218,6 +218,8 @@ def _get_path_with_real_case(filename):
             parts = parts.lower().split(os.path.sep)
 
             try:
+                if parts == ['']:
+                    return drive
                 return _resolve_listing(drive, iter(parts))
             except FileNotFoundError:
                 _listdir_cache.clear()
diff --git a/src/debugpy/_vendored/pydevd/tests_python/test_convert_utilities.py b/src/debugpy/_vendored/pydevd/tests_python/test_convert_utilities.py
index 28ffc7622..63f14e11b 100644
--- a/src/debugpy/_vendored/pydevd/tests_python/test_convert_utilities.py
+++ b/src/debugpy/_vendored/pydevd/tests_python/test_convert_utilities.py
@@ -5,6 +5,7 @@
 import io
 from _pydev_bundle.pydev_log import log_context
 import pytest
+import sys
 
 
 def test_convert_utilities(tmpdir):
@@ -99,6 +100,12 @@ def test_source_reference(tmpdir):
         assert pydevd_file_utils.get_server_filename_from_source_reference(source_reference) == '/another/my'
 
 
+@pytest.mark.skipif(sys.platform != 'win32', reason='Windows-only test.')
+def test_translate_only_drive():
+    import pydevd_file_utils
+    assert pydevd_file_utils.get_path_with_real_case('c:\\') == 'C:\\'
+
+
 def test_to_server_and_to_client(tmpdir):
     try: