diff --git a/monkey/monkey_island/cc/environment/data_dir_generator.py b/monkey/monkey_island/cc/environment/data_dir_generator.py
index 98907d639..58e16d4b7 100644
--- a/monkey/monkey_island/cc/environment/data_dir_generator.py
+++ b/monkey/monkey_island/cc/environment/data_dir_generator.py
@@ -1,14 +1,30 @@
+import logging
 import os
 
 from monkey_island.cc.environment.utils import is_windows_os
 from monkey_island.cc.environment.windows_permissions import set_full_folder_access
 
+LOG = logging.getLogger(__name__)
+
 
 def create_data_dir(data_dir: str, create_parent_dirs: bool) -> None:
     if not os.path.isdir(data_dir):
-        if create_parent_dirs:
-            os.makedirs(data_dir, mode=0o700)
-        else:
-            os.mkdir(data_dir, mode=0o700)
+        try:
+            if create_parent_dirs:
+                os.makedirs(data_dir, mode=0o700)
+            else:
+                os.mkdir(data_dir, mode=0o700)
+        except Exception as ex:
+            LOG.error(
+                f'Could not create data directory at "{data_dir}" (maybe `$HOME` could not be '
+                f"resolved?): {str(ex)}"
+            )
+
         if is_windows_os():  # `mode=0o700` doesn't work on Windows
-            set_full_folder_access(folder_path=data_dir)
+            try:
+                set_full_folder_access(folder_path=data_dir)
+            except Exception as ex:
+                LOG.error(
+                    f'Data directory was created at "{data_dir}" but permissions could not be '
+                    f"set successfully: {str(ex)}"
+                )