diff --git a/picard/ui/options/renaming.py b/picard/ui/options/renaming.py
index 0df1acbbf..3d6deac18 100644
--- a/picard/ui/options/renaming.py
+++ b/picard/ui/options/renaming.py
@@ -46,7 +46,7 @@ from picard.config import (
 )
 from picard.const.sys import IS_WIN
 from picard.script import ScriptParser
-from picard.util.filenaming import system_supports_long_paths
+from picard.util import system_supports_long_paths
 
 from picard.ui.options import (
     OptionsCheckError,
diff --git a/picard/util/__init__.py b/picard/util/__init__.py
index a986c2f25..57752c392 100644
--- a/picard/util/__init__.py
+++ b/picard/util/__init__.py
@@ -72,6 +72,9 @@ from picard.const.sys import (
 )
 
 
+if IS_WIN:
+    import winreg
+
 # Windows path length constraints:
 # the entire path's length
 WIN_MAX_FILEPATH_LEN = 259
@@ -175,12 +178,32 @@ def decode_filename(filename):
         return filename.decode(_io_encoding)
 
 
+def system_supports_long_paths():
+    if not IS_WIN:
+        return True
+    else:
+        try:
+            # Use cached value
+            return system_supports_long_paths._supported
+        except AttributeError:
+            pass
+        try:
+            with winreg.OpenKey(winreg.HKEY_LOCAL_MACHINE,
+                                r"SYSTEM\CurrentControlSet\Control\FileSystem") as key:
+                system_supports_long_paths._supported = winreg.QueryValueEx(key, "LongPathsEnabled")[0] == 1
+                return system_supports_long_paths._supported
+        except OSError:
+            log.info('Failed reading LongPathsEnabled from registry')
+            return False
+
+
 def normpath(path):
     path = os.path.normpath(path)
     # If the path is longer than 259 characters on Windows, prepend the \\?\
     # prefix. This enables access to long paths using the Windows API. See
     # https://docs.microsoft.com/en-us/windows/win32/fileio/maximum-file-path-limitation
-    if IS_WIN and len(path) > WIN_MAX_FILEPATH_LEN and not path.startswith(WIN_LONGPATH_PREFIX):
+    if (IS_WIN and len(path) > WIN_MAX_FILEPATH_LEN and not system_supports_long_paths()
+        and not path.startswith(WIN_LONGPATH_PREFIX)):
         path = WIN_LONGPATH_PREFIX + path
     try:
         path = os.path.realpath(path)
diff --git a/picard/util/filenaming.py b/picard/util/filenaming.py
index 5b2241793..a35ff4d4b 100644
--- a/picard/util/filenaming.py
+++ b/picard/util/filenaming.py
@@ -54,7 +54,6 @@ from picard.util import (
 
 win32api = None
 if IS_WIN:
-    import winreg
     try:
         import win32api  # isort:skip
         import pywintypes
@@ -150,25 +149,6 @@ def _shorten_to_bytes_length(text, length):  # noqa: E302
     return ""
 
 
-def system_supports_long_paths():
-    if not IS_WIN:
-        return True
-    else:
-        try:
-            # Use cached value
-            return system_supports_long_paths._supported
-        except AttributeError:
-            pass
-        try:
-            with winreg.OpenKey(winreg.HKEY_LOCAL_MACHINE,
-                                r"SYSTEM\CurrentControlSet\Control\FileSystem") as key:
-                system_supports_long_paths._supported = winreg.QueryValueEx(key, "LongPathsEnabled")[0] == 1
-                return system_supports_long_paths._supported
-        except OSError:
-            log.info('Failed reading LongPathsEnabled from registry')
-            return False
-
-
 class ShortenMode(IntEnum):
     BYTES = 0
     UTF16 = 1
diff --git a/test/test_utils.py b/test/test_utils.py
index 508385752..3571e12f0 100644
--- a/test/test_utils.py
+++ b/test/test_utils.py
@@ -37,7 +37,10 @@ import re
 import subprocess  # nosec: B404
 from tempfile import NamedTemporaryFile
 import unittest
-from unittest.mock import Mock
+from unittest.mock import (
+    Mock,
+    patch,
+)
 
 from test.picardtestcase import PicardTestCase
 
@@ -722,7 +725,9 @@ class NormpathTest(PicardTestCase):
         self.assertEqual('C:\\Bar.baz', normpath('C:/Foo/../Bar.baz'))
 
     @unittest.skipUnless(IS_WIN, "windows test")
-    def test_normpath_windows_longpath(self):
+    @patch.object(util, 'system_supports_long_paths')
+    def test_normpath_windows_longpath(self, mock_system_supports_long_paths):
+        mock_system_supports_long_paths.return_value = False
         path = 'C:\\foo\\' + (252 * 'a')
         self.assertEqual(path, normpath(path))
         path += 'a'