diff --git a/monkey/infection_monkey/exploit/tools/helpers.py b/monkey/infection_monkey/exploit/tools/helpers.py
index 87f5636eb..c287b0dbb 100644
--- a/monkey/infection_monkey/exploit/tools/helpers.py
+++ b/monkey/infection_monkey/exploit/tools/helpers.py
@@ -1,7 +1,7 @@
 import logging
 import random
 import string
-from pathlib import Path
+from pathlib import Path, PurePosixPath, PureWindowsPath
 from typing import Any, Mapping
 
 from infection_monkey.model import VictimHost
@@ -20,9 +20,9 @@ def get_random_file_suffix() -> str:
 
 def get_agent_dest_path(host: VictimHost, options: Mapping[str, Any]) -> Path:
     if host.os["type"] == "windows":
-        path = Path(options["dropper_target_path_win_64"])
+        path = PureWindowsPath(options["dropper_target_path_win_64"])
     else:
-        path = Path(options["dropper_target_path_linux"])
+        path = PurePosixPath(options["dropper_target_path_linux"])
 
     return _add_random_suffix(path)