diff --git a/app/commands/progress/sync/off.py b/app/commands/progress/sync/off.py
index 256e4f3..549c8ce 100644
--- a/app/commands/progress/sync/off.py
+++ b/app/commands/progress/sync/off.py
@@ -53,6 +53,7 @@ def off() -> None:
         local_progress = json.load(file)
 
     rmtree(PROGRESS_LOCAL_FOLDER_NAME)
+    os.makedirs(os.path.dirname(local_progress_filepath), exist_ok=True)
 
     # Re-create just the progress folder
     with open(local_progress_filepath, "a") as progress_file:
diff --git a/app/commands/progress/sync/on.py b/app/commands/progress/sync/on.py
index b879e08..6d5fdb5 100644
--- a/app/commands/progress/sync/on.py
+++ b/app/commands/progress/sync/on.py
@@ -69,6 +69,17 @@ def on() -> None:
 
     clone_with_custom_name(f"{username}/{fork_name}", PROGRESS_LOCAL_FOLDER_NAME)
 
+    # Verify clone succeeded, else restore local progress before failing
+    if not os.path.exists(PROGRESS_LOCAL_FOLDER_NAME):
+        os.makedirs(os.path.dirname(local_progress_filepath), exist_ok=True)
+        with open(local_progress_filepath, "w") as file:
+            file.write(json.dumps(local_progress, indent=2))
+        raise RuntimeError(
+            f"Clone failed for {PROGRESS_LOCAL_FOLDER_NAME}. "
+            "Your local progress has been restored."
+            "Re-run the command `gitmastery progress sync on` to try again."
+        )
+
     # To reconcile the difference between local and remote progress, we merge by
     # (exercise_name, start_time) which should be unique
     remote_progress = []
diff --git a/app/utils/cli.py b/app/utils/cli.py
index a49fdc8..fe24236 100644
--- a/app/utils/cli.py
+++ b/app/utils/cli.py
@@ -1,13 +1,35 @@
 import os
 import shutil
 import stat
+import time
 from pathlib import Path
 from typing import Union
 
+MAX_DELETE_RETRIES = 20
+MAX_RETRY_INTERVAL = 0.2
+
 
 def rmtree(folder_name: Union[str, Path]) -> None:
+    """
+    Remove a directory tree.
+
+    Raises RuntimeError if the folder still exists after max retries.
+    """
+    if not os.path.exists(folder_name):
+        return
+
     def force_remove_readonly(func, path, _):
         os.chmod(path, stat.S_IWRITE)
         func(path)
 
     shutil.rmtree(folder_name, onerror=force_remove_readonly)
+
+    # Wait for folder to be fully deleted (Windows can be slow with permissions)
+    max_retries = MAX_DELETE_RETRIES
+    for _ in range(max_retries):
+        if not os.path.exists(folder_name):
+            return
+        time.sleep(MAX_RETRY_INTERVAL)
+
+    # If folder still exists after retries, raise error
+    raise RuntimeError(f"Failed to delete {folder_name} after {max_retries} retries")