diff --git a/picard/ui/options/renaming.py b/picard/ui/options/renaming.py
index 3d6deac18..6615302d4 100644
--- a/picard/ui/options/renaming.py
+++ b/picard/ui/options/renaming.py
@@ -202,6 +202,20 @@ class RenamingOptionsPage(OptionsPage):
         if not IS_WIN:
             self.ui.windows_compatibility.setEnabled(active)
 
+    def toggle_windows_long_paths(self, state):
+        if state and not system_supports_long_paths():
+            dialog = QtWidgets.QMessageBox(
+                QtWidgets.QMessageBox.Icon.Information,
+                _('Windows long path support'),
+                _(
+                    'Enabling long paths on Windows might cause files being saved with path names '
+                    'exceeding the 259 character limit traditionally imposed by the Windows API. '
+                    'Some software might not be able to properly access those files.'
+                ),
+                QtWidgets.QMessageBox.StandardButton.Ok,
+                self)
+            dialog.exec_()
+
     def save_from_editor(self):
         self.script_text = self.script_editor_dialog.get_script()
         self.update_selector_from_editor()
@@ -238,6 +252,10 @@ class RenamingOptionsPage(OptionsPage):
 
     def load(self):
         config = get_config()
+        try:
+            self.ui.windows_long_paths.toggled.disconnect(self.toggle_windows_long_paths)
+        except TypeError:
+            pass
         if IS_WIN:
             self.ui.windows_compatibility.setChecked(True)
             self.ui.windows_compatibility.setEnabled(False)
@@ -259,6 +277,7 @@ class RenamingOptionsPage(OptionsPage):
         else:
             self.update_selector_from_settings()
         self.update_examples_from_local()
+        self.ui.windows_long_paths.toggled.connect(self.toggle_windows_long_paths)
 
     def check(self):
         self.check_format()