diff --git a/monkey/monkey_island/cc/server_utils/file_utils.py b/monkey/monkey_island/cc/server_utils/file_utils.py
index 25161ca2f..995501c09 100644
--- a/monkey/monkey_island/cc/server_utils/file_utils.py
+++ b/monkey/monkey_island/cc/server_utils/file_utils.py
@@ -55,11 +55,10 @@ def _create_secure_directory_windows(path: str):
 
 
 def get_file_descriptor_for_new_secure_file(path: str) -> int:
-    if not os.path.isfile(path):
-        if is_windows_os():
-            return _get_file_descriptor_for_new_secure_file_windows(path)
-        else:
-            return _get_file_descriptor_for_new_secure_file_linux(path)
+    if is_windows_os():
+        return _get_file_descriptor_for_new_secure_file_windows(path)
+    else:
+        return _get_file_descriptor_for_new_secure_file_linux(path)
 
 
 def _get_file_descriptor_for_new_secure_file_linux(path: str) -> int:
diff --git a/monkey/tests/unit_tests/monkey_island/cc/server_utils/test_file_utils.py b/monkey/tests/unit_tests/monkey_island/cc/server_utils/test_file_utils.py
index ac0c20abe..7e3e10ed6 100644
--- a/monkey/tests/unit_tests/monkey_island/cc/server_utils/test_file_utils.py
+++ b/monkey/tests/unit_tests/monkey_island/cc/server_utils/test_file_utils.py
@@ -98,8 +98,9 @@ def test_create_secure_directory__perm_windows(test_path):
 def test_create_secure_file__already_created(test_path):
     os.close(os.open(test_path, os.O_CREAT, stat.S_IRWXU))
     assert os.path.isfile(test_path)
-    # test fails if any exceptions are thrown
-    get_file_descriptor_for_new_secure_file(test_path)
+
+    with pytest.raises(Exception):
+        get_file_descriptor_for_new_secure_file(test_path)
 
 
 def test_create_secure_file__no_parent_dir(test_path_nested):