diff --git a/monkey/infection_monkey/dropper.py b/monkey/infection_monkey/dropper.py
index d76a7bc66..6407c08de 100644
--- a/monkey/infection_monkey/dropper.py
+++ b/monkey/infection_monkey/dropper.py
@@ -20,8 +20,11 @@ from infection_monkey.utils.file_utils import mark_file_for_deletion_on_windows
 
 if "win32" == sys.platform:
     from win32process import DETACHED_PROCESS
+
+    DATE_REFERENCE_PATH_WINDOWS = os.path.expandvars(WindowsPath(r"%windir%\system32\kernel32.dll"))
 else:
     DETACHED_PROCESS = 0
+    DATE_REFERENCE_PATH_LINUX = PosixPath("/bin/sh")
 
 # Linux doesn't have WindowsError
 try:
@@ -34,8 +37,6 @@ except NameError:
 logger = logging.getLogger(__name__)
 
 MOVEFILE_DELAY_UNTIL_REBOOT = 4
-DATE_REFERENCE_PATH_WINDOWS = WindowsPath(r"%windir%\system32\kernel32.dll")
-DATE_REFERENCE_PATH_LINUX = PosixPath("/bin/sh")
 
 
 class MonkeyDrops(object):
@@ -112,7 +113,7 @@ class MonkeyDrops(object):
                 return False
 
         if sys.platform == "win32":
-            dropper_date_reference_path = os.path.expandvars(DATE_REFERENCE_PATH_WINDOWS)
+            dropper_date_reference_path = DATE_REFERENCE_PATH_WINDOWS
         else:
             dropper_date_reference_path = DATE_REFERENCE_PATH_LINUX
 
diff --git a/monkey/infection_monkey/exploit/tools/helpers.py b/monkey/infection_monkey/exploit/tools/helpers.py
index 8334f33a6..0ce1c474e 100644
--- a/monkey/infection_monkey/exploit/tools/helpers.py
+++ b/monkey/infection_monkey/exploit/tools/helpers.py
@@ -10,8 +10,8 @@ logger = logging.getLogger(__name__)
 RAND_SUFFIX_LEN = 8
 
 # Where to upload agent binaries on victims
-AGENT_BINARY_PATH_LINUX = "/tmp/monkey"
-AGENT_BINARY_PATH_WIN64 = r"C:\Windows\temp\monkey64.exe"
+AGENT_BINARY_PATH_LINUX = PurePosixPath("/tmp/monkey")
+AGENT_BINARY_PATH_WIN64 = PureWindowsPath(r"C:\Windows\temp\monkey64.exe")
 
 
 def get_agent_dst_path(host: VictimHost) -> PurePath:
diff --git a/monkey/tests/unit_tests/infection_monkey/exploit/test_powershell.py b/monkey/tests/unit_tests/infection_monkey/exploit/test_powershell.py
index 24afebc85..c5d428f47 100644
--- a/monkey/tests/unit_tests/infection_monkey/exploit/test_powershell.py
+++ b/monkey/tests/unit_tests/infection_monkey/exploit/test_powershell.py
@@ -5,7 +5,7 @@ from unittest.mock import MagicMock
 import pytest
 
 from infection_monkey.exploit import powershell
-from infection_monkey.exploit.tools.helpers import AGENT_BINARY_PATH_WIN64, RAND_SUFFIX_LEN
+from infection_monkey.exploit.tools.helpers import AGENT_BINARY_PATH_WIN64
 from infection_monkey.model.host import VictimHost
 
 # Use the path_win32api_get_user_name fixture for all tests in this module
@@ -113,10 +113,7 @@ def test_successful_copy(monkeypatch, powershell_exploiter, powershell_arguments
 
     exploit_result = powershell_exploiter.exploit_host(**powershell_arguments)
 
-    # Check if the copied agent name has randomness of 8 plus dash
-    assert len(str(AGENT_BINARY_PATH_WIN64)) + RAND_SUFFIX_LEN + 1 == len(
-        str(mock_client.return_value.copy_file.call_args[0][1])
-    )
+    assert AGENT_BINARY_PATH_WIN64.stem in str(mock_client.return_value.copy_file.call_args[0][1])
     assert exploit_result.exploitation_success