diff --git a/cloudbaseinit/exception.py b/cloudbaseinit/exception.py
index f954b451..79edfb84 100644
--- a/cloudbaseinit/exception.py
+++ b/cloudbaseinit/exception.py
@@ -71,3 +71,14 @@ class WindowsCloudbaseInitException(CloudbaseInitException):
         except TypeError:
             formatted_msg = msg
         super(WindowsCloudbaseInitException, self).__init__(formatted_msg)
+
+
+class LoadUserProfileCloudbaseInitException(WindowsCloudbaseInitException):
+    """Windows cannot load the newly created user profile.
+
+    The load user profile can fail if the Windows subsystems responsible for
+    the action are not ready. This usually happens on laggy systems and should
+    be retried.
+    """
+
+    pass
diff --git a/cloudbaseinit/osutils/windows.py b/cloudbaseinit/osutils/windows.py
index 290c2e5a..5630d212 100644
--- a/cloudbaseinit/osutils/windows.py
+++ b/cloudbaseinit/osutils/windows.py
@@ -642,6 +642,9 @@ class WindowsUtils(base.BaseOSUtils):
             # User not found
             pass
 
+    @retry_decorator.retry_decorator(
+        max_retry_count=3,
+        exceptions=exception.LoadUserProfileCloudbaseInitException)
     def create_user_logon_session(self, username, password, domain='.',
                                   load_profile=True,
                                   logon_type=LOGON32_LOGON_INTERACTIVE):
@@ -666,7 +669,7 @@ class WindowsUtils(base.BaseOSUtils):
             ret_val = userenv.LoadUserProfileW(token, ctypes.byref(pi))
             if not ret_val:
                 kernel32.CloseHandle(token)
-                raise exception.WindowsCloudbaseInitException(
+                raise exception.LoadUserProfileCloudbaseInitException(
                     "Cannot load user profile: %r")
 
         return token
diff --git a/cloudbaseinit/tests/osutils/test_windows.py b/cloudbaseinit/tests/osutils/test_windows.py
index ce3a0cf7..a9eec533 100644
--- a/cloudbaseinit/tests/osutils/test_windows.py
+++ b/cloudbaseinit/tests/osutils/test_windows.py
@@ -452,7 +452,9 @@ class TestWindowsUtils(testutils.CloudbaseInitTestBase):
         self._test_create_user(fail=True)
 
     @mock.patch('cloudbaseinit.osutils.windows.Win32_PROFILEINFO')
-    def _test_create_user_logon_session(self, mock_Win32_PROFILEINFO, logon,
+    @mock.patch('time.sleep')
+    def _test_create_user_logon_session(self, mock_time_sleep,
+                                        mock_Win32_PROFILEINFO, logon,
                                         loaduser, load_profile=True,
                                         last_error=None):
         self._wintypes_mock.HANDLE = mock.MagicMock()
@@ -474,7 +476,9 @@ class TestWindowsUtils(testutils.CloudbaseInitTestBase):
             userenv.LoadUserProfileW.return_value = None
             kernel32.CloseHandle.return_value = None
             with self.assert_raises_windows_message(
-                    "Cannot load user profile: %r", last_error):
+                    "Cannot load user profile: %r", last_error,
+                    get_last_error_called_times=4,
+                    format_error_called_times=4):
                 self._winutils.create_user_logon_session(
                     self._USERNAME, self._PASSWORD, domain='.',
                     load_profile=load_profile)
diff --git a/cloudbaseinit/tests/testutils.py b/cloudbaseinit/tests/testutils.py
index a3e3303b..fdea01c3 100644
--- a/cloudbaseinit/tests/testutils.py
+++ b/cloudbaseinit/tests/testutils.py
@@ -159,7 +159,9 @@ class CloudbaseInitTestBase(unittest.TestCase):
     @contextlib.contextmanager
     def assert_raises_windows_message(
             self, expected_msg, error_code,
-            exc=exception.WindowsCloudbaseInitException):
+            exc=exception.WindowsCloudbaseInitException,
+            get_last_error_called_times=1,
+            format_error_called_times=1):
         """Helper method for testing raised error messages
 
         This assert method is similar to :meth:`~assertRaises`, but
@@ -188,11 +190,16 @@ class CloudbaseInitTestBase(unittest.TestCase):
             # This can be called when the error code is not given,
             # but we don't have control over that, so test that
             # it's actually called only once.
-            mock_get_last_error.assert_called_once_with()
-            mock_format_error.assert_called_once_with(
+            mock_get_last_error.assert_called()
+            self.assertEqual(mock_get_last_error.call_count,
+                             get_last_error_called_times)
+            mock_format_error.assert_called_with(
                 mock_get_last_error.return_value)
         else:
-            mock_format_error.assert_called_once_with(error_code)
+            mock_format_error.assert_called_with(error_code)
+
+        self.assertEqual(mock_format_error.call_count,
+                         format_error_called_times)
 
         expected_msg = expected_msg % mock_format_error.return_value
         self.assertEqual(expected_msg, cm.exception.args[0])