diff --git a/monkey/tests/unit_tests/monkey_island/cc/setup/test_island_config_options_validator.py b/monkey/tests/unit_tests/monkey_island/cc/setup/test_island_config_options_validator.py
index 1b1be6718..e3984099c 100644
--- a/monkey/tests/unit_tests/monkey_island/cc/setup/test_island_config_options_validator.py
+++ b/monkey/tests/unit_tests/monkey_island/cc/setup/test_island_config_options_validator.py
@@ -1,4 +1,5 @@
 import os
+import subprocess
 
 import pytest
 
@@ -7,15 +8,19 @@ from monkey_island.cc.setup.island_config_options import IslandConfigOptions
 from monkey_island.cc.setup.island_config_options_validator import raise_on_invalid_options
 
 
+LINUX_READ_ONLY_BY_USER = 0o400
+LINUX_RWX_BY_ALL = 0o777
+
 @pytest.fixture
-def island_config_options(tmpdir, create_empty_file):
+def linux_island_config_options(tmpdir, create_empty_file):
     crt_file = os.path.join(tmpdir, "test.crt")
     create_empty_file(crt_file)
-    os.chmod(crt_file, 0o400)
+    os.chmod(crt_file, LINUX_READ_ONLY_BY_USER)
 
     key_file = os.path.join(tmpdir, "test.key")
     create_empty_file(key_file)
-    os.chmod(key_file, 0o400)
+    os.chmod(key_file, LINUX_READ_ONLY_BY_USER)
+
     return IslandConfigOptions(
         {
             "ssl_certificate": {
@@ -27,41 +32,114 @@ def island_config_options(tmpdir, create_empty_file):
 
 
 @pytest.mark.skipif(os.name != "posix", reason="Tests Posix (not Windows) permissions.")
-def test_valid_crt_and_key_paths(island_config_options):
+def test_linux_valid_crt_and_key_paths(linux_island_config_options):
     try:
-        raise_on_invalid_options(island_config_options)
+        raise_on_invalid_options(linux_island_config_options)
     except Exception as ex:
         print(ex)
         assert False
 
 
 @pytest.mark.skipif(os.name != "posix", reason="Tests Posix (not Windows) permissions.")
-def test_crt_path_does_not_exist(island_config_options):
-    os.remove(island_config_options.crt_path)
+def test_linux_crt_path_does_not_exist(linux_island_config_options):
+    os.remove(linux_island_config_options.crt_path)
 
     with pytest.raises(FileNotFoundError):
-        raise_on_invalid_options(island_config_options)
+        raise_on_invalid_options(linux_island_config_options)
 
 
 @pytest.mark.skipif(os.name != "posix", reason="Tests Posix (not Windows) permissions.")
-def test_crt_path_insecure_permissions(island_config_options):
-    os.chmod(island_config_options.crt_path, 0o777)
+def test_linux_crt_path_insecure_permissions(linux_island_config_options):
+    os.chmod(linux_island_config_options.crt_path, LINUX_RWX_BY_ALL)
 
     with pytest.raises(InsecurePermissionsError):
-        raise_on_invalid_options(island_config_options)
+        raise_on_invalid_options(linux_island_config_options)
 
 
 @pytest.mark.skipif(os.name != "posix", reason="Tests Posix (not Windows) permissions.")
-def test_key_path_does_not_exist(island_config_options):
-    os.remove(island_config_options.key_path)
+def test_linux_key_path_does_not_exist(linux_island_config_options):
+    os.remove(linux_island_config_options.key_path)
 
     with pytest.raises(FileNotFoundError):
-        raise_on_invalid_options(island_config_options)
+        raise_on_invalid_options(linux_island_config_options)
 
 
 @pytest.mark.skipif(os.name != "posix", reason="Tests Posix (not Windows) permissions.")
-def test_key_path_insecure_permissions(island_config_options):
-    os.chmod(island_config_options.key_path, 0o777)
+def test_linux_key_path_insecure_permissions(linux_island_config_options):
+    os.chmod(linux_island_config_options.key_path, LINUX_RWX_BY_ALL)
 
     with pytest.raises(InsecurePermissionsError):
-        raise_on_invalid_options(island_config_options)
+        raise_on_invalid_options(linux_island_config_options)
+
+
+@pytest.fixture
+def windows_island_config_options(tmpdir, create_empty_file):
+    crt_file = os.path.join(tmpdir, "test.crt")
+    create_empty_file(crt_file)
+    cmd_to_change_permissions = get_windows_cmd_to_change_permissions(crt_file, 'R')
+    subprocess.run(cmd_to_change_permissions, shell=True)
+
+    key_file = os.path.join(tmpdir, "test.key")
+    create_empty_file(key_file)
+    cmd_to_change_permissions = get_windows_cmd_to_change_permissions(key_file, 'R')
+    subprocess.run(cmd_to_change_permissions, shell=True)
+
+    return IslandConfigOptions(
+        {
+            "ssl_certificate": {
+                "ssl_certificate_file": crt_file,
+                "ssl_certificate_key_file": key_file,
+            }
+        }
+    )
+
+
+def get_windows_cmd_to_change_permissions(file_name, permissions):
+    """
+    :param file_name: name of file
+    :param permissions: can be: N (None), R (Read), W (Write), C (Change (write)), F (Full control)
+    """
+    return f"echo y| cacls {file_name} /p %USERNAME%:{permissions}"
+
+
+@pytest.mark.skipif(os.name == "posix", reason="Tests Windows (not Posix) permissions.")
+def test_windows_valid_crt_and_key_paths(windows_island_config_options):
+    try:
+        raise_on_invalid_options(windows_island_config_options)
+    except Exception as ex:
+        print(ex)
+        assert False
+
+
+@pytest.mark.skipif(os.name == "posix", reason="Tests Windows (not Posix) permissions.")
+def test_windows_crt_path_does_not_exist(windows_island_config_options):
+    os.remove(windows_island_config_options.crt_path)
+
+    with pytest.raises(FileNotFoundError):
+        raise_on_invalid_options(windows_island_config_options)
+
+
+@pytest.mark.skipif(os.name == "posix", reason="Tests Windows (not Posix) permissions.")
+def test_windows_crt_path_insecure_permissions(windows_island_config_options):
+    cmd_to_change_permissions = get_windows_cmd_to_change_permissions(windows_island_config_options.crt_path, 'W')
+    subprocess.run(cmd_to_change_permissions, shell=True)
+
+    with pytest.raises(InsecurePermissionsError):
+        raise_on_invalid_options(windows_island_config_options)
+
+
+@pytest.mark.skipif(os.name == "posix", reason="Tests Windows (not Posix) permissions.")
+def test_windows_key_path_does_not_exist(windows_island_config_options):
+    os.remove(windows_island_config_options.key_path)
+
+    with pytest.raises(FileNotFoundError):
+        raise_on_invalid_options(windows_island_config_options)
+
+
+@pytest.mark.skipif(os.name == "posix", reason="Tests Windows (not Posix) permissions.")
+def test_windows_key_path_insecure_permissions(windows_island_config_options):
+    cmd_to_change_permissions = get_windows_cmd_to_change_permissions(windows_island_config_options.key_path, 'W')
+    subprocess.run(cmd_to_change_permissions, shell=True)
+
+    with pytest.raises(InsecurePermissionsError):
+        raise_on_invalid_options(windows_island_config_options)