diff --git a/src/documents/models.py b/src/documents/models.py
index 39dcc4a37..17357c1a7 100644
--- a/src/documents/models.py
+++ b/src/documents/models.py
@@ -415,7 +415,10 @@ class Document(models.Model):
 
 def try_delete_empty_directories(directory):
     # Go up in the directory hierarchy and try to delete all directories
-    while directory != Document.filename_to_path(""):
+    directory = os.path.normpath(directory)
+    root = os.path.normpath(Document.filename_to_path(""))
+
+    while directory != root:
         # Try to delete the current directory
         try:
             os.rmdir(directory)
@@ -425,6 +428,7 @@ def try_delete_empty_directories(directory):
 
         # Cut off actual directory and go one level up
         directory, _ = os.path.split(directory)
+        directory = os.path.normpath(directory)
 
 
 @receiver(models.signals.m2m_changed, sender=Document.tags.through)
diff --git a/src/documents/tests/test_file_handling.py b/src/documents/tests/test_file_handling.py
index f6c8d0eba..fae1c0634 100644
--- a/src/documents/tests/test_file_handling.py
+++ b/src/documents/tests/test_file_handling.py
@@ -319,7 +319,7 @@ class TestDate(TestCase):
         self.assertEqual(os.path.isdir(settings.MEDIA_ROOT +
                          "/documents/originals/none"), False)
         self.assertEqual(os.path.isdir(settings.MEDIA_ROOT +
-                         "/documents/originals"), False)
+                         "/documents/originals"), True)
 
     @override_settings(MEDIA_ROOT="/tmp/paperless-tests-{}".
                        format(str(uuid4())[:8]))