diff --git a/monkey/monkey_island/cc/repository/file_storage/i_file_repository.py b/monkey/monkey_island/cc/repository/file_storage/i_file_repository.py
index cfebe5c05..c0897aa1a 100644
--- a/monkey/monkey_island/cc/repository/file_storage/i_file_repository.py
+++ b/monkey/monkey_island/cc/repository/file_storage/i_file_repository.py
@@ -56,5 +56,7 @@ class IFileRepository(metaclass=abc.ABCMeta):
     def delete_all_files(self):
         """
         Delete all files that have been stored using this service.
+
+        :raises RemovalError: If an error was encountered while attempting to remove a file
         """
         pass
diff --git a/monkey/monkey_island/cc/repository/file_storage/local_storage_file_repository.py b/monkey/monkey_island/cc/repository/file_storage/local_storage_file_repository.py
index d18e029f4..564582c76 100644
--- a/monkey/monkey_island/cc/repository/file_storage/local_storage_file_repository.py
+++ b/monkey/monkey_island/cc/repository/file_storage/local_storage_file_repository.py
@@ -82,6 +82,9 @@ class LocalStorageFileRepository(IFileRepository):
         return safe_file_path
 
     def delete_all_files(self):
-        for file in get_all_regular_files_in_directory(self._storage_directory):
-            logger.debug(f"Deleting {file}")
-            file.unlink()
+        try:
+            for file in get_all_regular_files_in_directory(self._storage_directory):
+                logger.debug(f"Deleting {file}")
+                file.unlink()
+        except Exception as err:
+            raise RemovalError(f"Error while attempting to clear the repository: {err}")