diff --git a/monkey/common/utils/attack_utils.py b/monkey/common/utils/attack_utils.py
index d86b0ba55..f1d4e21b0 100644
--- a/monkey/common/utils/attack_utils.py
+++ b/monkey/common/utils/attack_utils.py
@@ -12,8 +12,8 @@ class ScanStatus(Enum):
 
 class UsageEnum(Enum):
     SMB = {
-        ScanStatus.USED.value: "SMB exploiter ran the monkey by creating a service via MS-SCMR.",
-        ScanStatus.SCANNED.value: "SMB exploiter failed to run the monkey by creating a service "
+        ScanStatus.USED.value: "SMB exploiter ran the agent by creating a service via MS-SCMR.",
+        ScanStatus.SCANNED.value: "SMB exploiter failed to run the agent by creating a service "
         "via MS-SCMR.",
     }
     MIMIKATZ = {
@@ -24,19 +24,19 @@ class UsageEnum(Enum):
         ScanStatus.USED.value: "WinAPI was called to load mimikatz.",
         ScanStatus.SCANNED.value: "Monkey tried to call WinAPI to load mimikatz.",
     }
-    DROPPER = {
-        ScanStatus.USED.value: "WinAPI was used to mark monkey files for deletion on next boot."
+    AGENT_WINAPI = {
+        ScanStatus.USED.value: "WinAPI was used to mark agent's files for deletion on next boot."
     }
     SINGLETON_WINAPI = {
-        ScanStatus.USED.value: "WinAPI was called to acquire system singleton for monkey's "
+        ScanStatus.USED.value: "WinAPI was called to acquire system singleton for agent's "
         "process.",
         ScanStatus.SCANNED.value: "WinAPI call to acquire system singleton"
-        " for monkey process wasn't successful.",
+        " for agent's process wasn't successful.",
     }
     DROPPER_WINAPI = {
-        ScanStatus.USED.value: "WinAPI was used to mark monkey files for deletion on next boot."
+        ScanStatus.USED.value: "WinAPI was used to mark dropper files for deletion on next boot."
     }
 
 
 # Dict that describes what BITS job was used for
-BITS_UPLOAD_STRING = "BITS job was used to upload monkey to a remote system."
+BITS_UPLOAD_STRING = "BITS job was used to upload agent to a remote system."
diff --git a/monkey/infection_monkey/dropper.py b/monkey/infection_monkey/dropper.py
index 90d6712d5..4bbc272ea 100644
--- a/monkey/infection_monkey/dropper.py
+++ b/monkey/infection_monkey/dropper.py
@@ -1,5 +1,4 @@
 import argparse
-import ctypes
 import filecmp
 import logging
 import os
@@ -8,17 +7,17 @@ import shutil
 import subprocess
 import sys
 import time
-from ctypes import c_char_p
+from pathlib import WindowsPath
 
-from common.utils.attack_utils import ScanStatus, UsageEnum
+from common.utils.attack_utils import UsageEnum
 from infection_monkey.config import WormConfiguration
-from infection_monkey.telemetry.attack.t1106_telem import T1106Telem
 from infection_monkey.utils.commands import (
     build_monkey_commandline_explicitly,
     get_monkey_commandline_linux,
     get_monkey_commandline_windows,
 )
 from infection_monkey.utils.environment import is_windows_os
+from infection_monkey.utils.file_utils import mark_file_for_deletion_on_windows
 
 if "win32" == sys.platform:
     from win32process import DETACHED_PROCESS
@@ -198,23 +197,9 @@ class MonkeyDrops(object):
                     )
 
                     # mark the file for removal on next boot
-                    dropper_source_path_ctypes = c_char_p(self._config["source_path"].encode())
-                    if 0 == ctypes.windll.kernel32.MoveFileExA(
-                        dropper_source_path_ctypes, None, MOVEFILE_DELAY_UNTIL_REBOOT
-                    ):
-                        logger.debug(
-                            "Error marking source file '%s' for deletion on next boot (error "
-                            "%d)",
-                            self._config["source_path"],
-                            ctypes.windll.kernel32.GetLastError(),
-                        )
-                    else:
-                        logger.debug(
-                            "Dropper source file '%s' is marked for deletion on next boot",
-                            self._config["source_path"],
-                        )
-                        T1106Telem(ScanStatus.USED, UsageEnum.DROPPER_WINAPI).send()
-
+                    mark_file_for_deletion_on_windows(
+                        WindowsPath(self._config["source_path"]), UsageEnum.DROPPER_WINAPI
+                    )
             logger.info("Dropper cleanup complete")
         except AttributeError:
             logger.error("Invalid configuration options. Failing")
diff --git a/monkey/infection_monkey/monkey.py b/monkey/infection_monkey/monkey.py
index e31c62cad..7f09adde4 100644
--- a/monkey/infection_monkey/monkey.py
+++ b/monkey/infection_monkey/monkey.py
@@ -3,7 +3,7 @@ import logging
 import os
 import subprocess
 import sys
-from pathlib import Path
+from pathlib import Path, WindowsPath
 from typing import List
 
 import infection_monkey.tunnel as tunnel
@@ -70,6 +70,7 @@ from infection_monkey.telemetry.state_telem import StateTelem
 from infection_monkey.telemetry.tunnel_telem import TunnelTelem
 from infection_monkey.utils.aws_environment_check import run_aws_environment_check
 from infection_monkey.utils.environment import is_windows_os
+from infection_monkey.utils.file_utils import mark_file_for_deletion_on_windows
 from infection_monkey.utils.monkey_dir import (
     create_monkey_dir,
     get_monkey_dir_path,
@@ -410,6 +411,9 @@ class InfectionMonkey:
 
         try:
             if "win32" == sys.platform:
+                mark_file_for_deletion_on_windows(
+                    WindowsPath(sys.executable), UsageEnum.AGENT_WINAPI
+                )
                 InfectionMonkey._self_delete_windows()
             else:
                 InfectionMonkey._self_delete_linux()
diff --git a/monkey/infection_monkey/payload/ransomware/file_selectors.py b/monkey/infection_monkey/payload/ransomware/file_selectors.py
index 1857d7d63..901b6b571 100644
--- a/monkey/infection_monkey/payload/ransomware/file_selectors.py
+++ b/monkey/infection_monkey/payload/ransomware/file_selectors.py
@@ -3,7 +3,7 @@ from pathlib import Path
 from typing import Iterable, Set
 
 from common.utils.file_utils import get_all_regular_files_in_directory
-from infection_monkey.utils.dir_utils import (
+from infection_monkey.utils.file_utils import (
     file_extension_filter,
     filter_files,
     is_not_shortcut_filter,
diff --git a/monkey/infection_monkey/utils/dir_utils.py b/monkey/infection_monkey/utils/dir_utils.py
deleted file mode 100644
index 9cd20a316..000000000
--- a/monkey/infection_monkey/utils/dir_utils.py
+++ /dev/null
@@ -1,27 +0,0 @@
-from pathlib import Path
-from typing import Callable, Iterable, Set
-
-
-def filter_files(
-    files: Iterable[Path], file_filters: Iterable[Callable[[Path], bool]]
-) -> Iterable[Path]:
-    filtered_files = files
-    for file_filter in file_filters:
-        filtered_files = filter(file_filter, filtered_files)
-
-    return filtered_files
-
-
-def file_extension_filter(file_extensions: Set) -> Callable[[Path], bool]:
-    def inner_filter(f: Path) -> bool:
-        return f.suffix in file_extensions
-
-    return inner_filter
-
-
-def is_not_symlink_filter(f: Path) -> bool:
-    return not f.is_symlink()
-
-
-def is_not_shortcut_filter(f: Path) -> bool:
-    return f.suffix != ".lnk"
diff --git a/monkey/infection_monkey/utils/file_utils.py b/monkey/infection_monkey/utils/file_utils.py
new file mode 100644
index 000000000..66235b9b1
--- /dev/null
+++ b/monkey/infection_monkey/utils/file_utils.py
@@ -0,0 +1,55 @@
+import ctypes
+import logging
+from pathlib import Path, WindowsPath
+from typing import Callable, Iterable, Set
+
+from common.utils.attack_utils import ScanStatus, UsageEnum
+
+logger = logging.getLogger(__name__)
+
+MOVEFILE_DELAY_UNTIL_REBOOT = 4
+
+
+def filter_files(
+    files: Iterable[Path], file_filters: Iterable[Callable[[Path], bool]]
+) -> Iterable[Path]:
+    filtered_files = files
+    for file_filter in file_filters:
+        filtered_files = filter(file_filter, filtered_files)
+
+    return filtered_files
+
+
+def file_extension_filter(file_extensions: Set) -> Callable[[Path], bool]:
+    def inner_filter(f: Path) -> bool:
+        return f.suffix in file_extensions
+
+    return inner_filter
+
+
+def is_not_symlink_filter(f: Path) -> bool:
+    return not f.is_symlink()
+
+
+def is_not_shortcut_filter(f: Path) -> bool:
+    return f.suffix != ".lnk"
+
+
+def mark_file_for_deletion_on_windows(file_path: WindowsPath, usage: UsageEnum):
+    from infection_monkey.telemetry.attack.t1106_telem import T1106Telem
+
+    file_source_path_ctypes = ctypes.c_char_p(str(file_path).encode())
+
+    mark_file_response = ctypes.windll.kernel32.MoveFileExA(
+        file_source_path_ctypes, None, MOVEFILE_DELAY_UNTIL_REBOOT
+    )
+
+    if mark_file_response == 0:
+        logger.debug(
+            f"Error marking file {file_path} for deletion on next boot:"
+            f"{ctypes.windll.kernel32.GetLastError()}"
+        )
+        return
+
+    logger.debug(f"File {file_path} is marked for deletion on next boot")
+    T1106Telem(ScanStatus.USED, usage).send()
diff --git a/monkey/tests/unit_tests/infection_monkey/utils/__init__.py b/monkey/tests/unit_tests/infection_monkey/utils/__init__.py
new file mode 100644
index 000000000..e69de29bb
diff --git a/monkey/tests/unit_tests/infection_monkey/utils/test_dir_utils.py b/monkey/tests/unit_tests/infection_monkey/utils/test_file_utils.py
similarity index 98%
rename from monkey/tests/unit_tests/infection_monkey/utils/test_dir_utils.py
rename to monkey/tests/unit_tests/infection_monkey/utils/test_file_utils.py
index fe7b499bf..2154f2c9e 100644
--- a/monkey/tests/unit_tests/infection_monkey/utils/test_dir_utils.py
+++ b/monkey/tests/unit_tests/infection_monkey/utils/test_file_utils.py
@@ -4,7 +4,7 @@ import pytest
 from tests.utils import add_files_to_dir, is_user_admin
 
 from common.utils.file_utils import get_all_regular_files_in_directory
-from infection_monkey.utils.dir_utils import (
+from infection_monkey.utils.file_utils import (
     file_extension_filter,
     filter_files,
     is_not_shortcut_filter,
diff --git a/monkey/tests/unit_tests/monkey_island/cc/server_utils/__init__.py b/monkey/tests/unit_tests/monkey_island/cc/server_utils/__init__.py
new file mode 100644
index 000000000..e69de29bb