diff --git a/oschmod/__init__.py b/oschmod/__init__.py
index 1e75830..1f1e035 100644
--- a/oschmod/__init__.py
+++ b/oschmod/__init__.py
@@ -31,7 +31,9 @@
 import re
 import stat
 import string
+import sys
 
+PATHLIB_ERROR = "Pathlib not supported for <py34. Version found: {}"
 IS_WINDOWS = platform.system() == 'Windows'
 HAS_PYWIN32 = False
 try:
@@ -335,7 +337,6 @@ def convert_stat_to_win(mode, user_type, object_type):
 
     return win_perm
 
-
 def win_get_user_type(sid, sids):
     """Given object and SIDs, return user type."""
     if sid == sids[OWNER]:
@@ -360,8 +361,9 @@ def win_get_permissions(path):
     """Get the file or dir permissions."""
     if not os.path.exists(path):
         raise FileNotFoundError('Path %s could not be found.' % path)
+    str_path = _win_transform_pathlib_to_str(path)
 
-    return _win_get_permissions(path, get_object_type(path))
+    return _win_get_permissions(str_path, get_object_type(path))
 
 
 def _get_basic_symbol_to_mode(symbol):
@@ -399,8 +401,9 @@ def win_set_permissions(path, mode):
     """Set the file or dir permissions."""
     if not os.path.exists(path):
         raise FileNotFoundError('Path %s could not be found.' % path)
+    str_path = _win_transform_pathlib_to_str(path)
 
-    _win_set_permissions(path, mode, get_object_type(path))
+    _win_set_permissions(str_path, mode, get_object_type(path))
 
 
 def _win_set_permissions(path, mode, object_type):
@@ -447,6 +450,22 @@ def _win_set_permissions(path, mode, object_type):
         path, win32security.DACL_SECURITY_INFORMATION, sec_des)
 
 
+def _win_transform_pathlib_to_str(path):
+    """Transform pathlib.WindowsPath to a string to support win32security
+    operations when getting and setting permissions.
+    """
+    # pathlib not available for <py34, primarily covering for py27
+    # sys.version_info implemented differently in py26 so use string.find()
+    py_version = sys.version
+    if py_version.startswith("2.6"):
+        raise RuntimeError(PATHLIB_ERROR.format(py_version))
+    elif sys.version_info.major < 3:
+        raise RuntimeError(PATHLIB_ERROR.format(py_version))
+    elif sys.version_info.minor < 4:
+        raise RuntimeError(PATHLIB_ERROR.format(py_version))
+    return "{}".format(path)
+
+
 def print_win_inheritance(flags):
     """Display inheritance flags."""
     print("  -Flags:", hex(flags))
diff --git a/requirements/test.txt b/requirements/test.txt
index f8a4d8d..54498be 100644
--- a/requirements/test.txt
+++ b/requirements/test.txt
@@ -1,2 +1,3 @@
+mock==4.0.3
 pytest==6.1.2
 pywin32==301;platform_system=="Windows"
diff --git a/tests/test_oschmod_pathlib.py b/tests/test_oschmod_pathlib.py
new file mode 100644
index 0000000..a4a33d9
--- /dev/null
+++ b/tests/test_oschmod_pathlib.py
@@ -0,0 +1,73 @@
+"""Unit tests for operations that might fail due to using Pathlib"""
+
+import mock
+import pytest
+
+import oschmod
+
+@mock.patch('oschmod._win_get_permissions')
+@mock.patch('oschmod._win_transform_pathlib_to_str')
+def test_win_get_permissions(transform_mock, get_permissions_mock):
+    oschmod.win_get_permissions('.')
+
+    transform_mock.assert_called_once_with('.')
+
+
+@mock.patch('oschmod._win_set_permissions')
+@mock.patch('oschmod._win_transform_pathlib_to_str')
+def test_win_set_permissions(transform_mock, set_permissions_mock):
+    oschmod.win_set_permissions('.', "mock_mode")
+
+    transform_mock.assert_called_once_with('.')
+
+
+@mock.patch('oschmod.sys')
+def test_win_transform_pathlib_to_str_negative_py26(mock_sys):
+    """Tests versions that do not support pathlib throws an exception.
+    py26 sys.version_info implemented different from >py26"""
+
+    mock_sys.version = '2.6.0'
+
+    with pytest.raises(RuntimeError, match='Pathlib not supported for <py34.'):
+        oschmod._win_transform_pathlib_to_str('mock_path')
+
+    mock_sys.version_info.assert_not_called()
+
+
+@pytest.mark.parametrize(
+    'major_version, minor_version',
+    [(2, 7), (2, 9), (3, 2), (3, 3)],
+)
+@mock.patch('oschmod.sys')
+def test_win_transform_pathlib_to_str_negative(
+    mock_sys, major_version, minor_version
+):
+    """Tests versions that do not support pathlib throws an exception.
+    py27 is the only supported version by lib, but testing other edge
+    cases as well
+    """
+    mock_sys.version = '{}.{}'.format(major_version, minor_version)
+    mock_sys.version_info.major = major_version
+    mock_sys.version_info.minor = minor_version
+
+    with pytest.raises(RuntimeError, match='Pathlib not supported for <py34.'):
+        oschmod._win_transform_pathlib_to_str('mock_path')
+
+
+@pytest.mark.parametrize(
+    'major_version, minor_version',
+    [(3, 5), (3, 6), (3, 7), (3, 8)],
+)
+@mock.patch('oschmod.sys')
+def test_win_transform_pathlib_to_str_positive(
+    mock_sys, major_version, minor_version
+):
+    """Tests pathlib is transformed into a string for windows for
+    supported versions."""
+    mock_sys.version = '{}.{}'.format(major_version, minor_version)
+    mock_sys.version_info.major = major_version
+    mock_sys.version_info.minor = minor_version
+
+    actual_path = oschmod._win_transform_pathlib_to_str('mock_path')
+
+    assert actual_path == 'mock_path'