diff --git a/.bin/Scripts/functions/cleanup.py b/.bin/Scripts/functions/cleanup.py
index 84227b30..cb400510 100644
--- a/.bin/Scripts/functions/cleanup.py
+++ b/.bin/Scripts/functions/cleanup.py
@@ -38,10 +38,7 @@ def cleanup_adwcleaner():
         shutil.move(source_quarantine, dest_name)
 
     # Delete source folder if empty
-    try:
-        os.rmdir(source_path)
-    except OSError:
-        pass
+    delete_empty_folders(source_path)
 
     # Main folder
     if os.path.exists(source_path):
@@ -139,11 +136,7 @@ def cleanup_d7ii():
                 shutil.move(entry.path, dest_path)
 
             # Remove folder
-            try:
-                os.rmdir(entry.path)
-            except OSError:
-                # Folder should be empty but whatever
-                pass
+            delete_empty_folders(entry.path)
 
     # Registry Items
     for key, settings in D7_HKCR_CLEANUP.items():
@@ -176,10 +169,7 @@ def cleanup_desktop():
             shutil.move(entry.path, dest_name)
 
     # Remove dir if empty
-    try:
-        os.rmdir(dest_folder)
-    except OSError:
-        pass
+    delete_empty_folders(dest_folder)
 
 def cleanup_emsisoft():
     """Remove EmsisoftCmd files from drive root."""
@@ -218,9 +208,23 @@ def cleanup_regbackups():
         shutil.move(entry.path, dest_path)
 
     # Delete source folders if empty
+    delete_empty_folders(r'{}\Support'.format(
+        global_vars['Env']['SYSTEMDRIVE']))
+
+def delete_empty_folders(folder_path):
+    """Delete all empty folders in path (depth first)."""
+    if not os.path.exists(folder_path) or not os.path.isdir(folder_path):
+        # Bail early (silently)
+        return
+
+    # Delete empty subfolders first
+    for item in os.scandir(folder_path):
+        if item.is_dir():
+            delete_empty_folders(item.path)
+
+    # Remove top folder
     try:
-        os.rmdir(source_path)
-        os.rmdir(r'{}\Support'.format(global_vars['Env']['SYSTEMDRIVE']))
+        os.rmdir(folder_path)
     except OSError:
         pass