diff --git a/monkey/infection_monkey/exploit/smbexec.py b/monkey/infection_monkey/exploit/smbexec.py
index 109771bd4..2afc74439 100644
--- a/monkey/infection_monkey/exploit/smbexec.py
+++ b/monkey/infection_monkey/exploit/smbexec.py
@@ -87,13 +87,13 @@ class SMBExploiter(HostExploiter):
             return self.exploit_result
 
         # execute the remote dropper in case the path isn't final
-        if remote_full_path.lower() != dest_path.lower():
+        if remote_full_path.lower() != str(dest_path).lower():
             cmdline = DROPPER_CMDLINE_DETACHED_WINDOWS % {
                 "dropper_path": remote_full_path
             } + build_monkey_commandline(
                 self.host,
                 self.current_depth - 1,
-                dest_path,
+                str(dest_path),
             )
         else:
             cmdline = MONKEY_CMDLINE_DETACHED_WINDOWS % {