diff --git a/picard/ui/ui_options_renaming.py b/picard/ui/ui_options_renaming.py
index 4c54c1db7..756f2a936 100644
--- a/picard/ui/ui_options_renaming.py
+++ b/picard/ui/ui_options_renaming.py
@@ -55,16 +55,13 @@ class Ui_RenamingOptionsPage(object):
         self.ascii_filenames = QtWidgets.QCheckBox(RenamingOptionsPage)
         self.ascii_filenames.setObjectName("ascii_filenames")
         self.verticalLayout_5.addWidget(self.ascii_filenames)
-        self.windows_compatibility = QtWidgets.QGroupBox(RenamingOptionsPage)
-        self.windows_compatibility.setCheckable(True)
-        self.windows_compatibility.setChecked(False)
+        self.windows_compatibility = QtWidgets.QCheckBox(RenamingOptionsPage)
         self.windows_compatibility.setObjectName("windows_compatibility")
-        self.verticalLayout_2 = QtWidgets.QVBoxLayout(self.windows_compatibility)
-        self.verticalLayout_2.setObjectName("verticalLayout_2")
-        self.windows_long_paths = QtWidgets.QCheckBox(self.windows_compatibility)
-        self.windows_long_paths.setObjectName("windows_long_paths")
-        self.verticalLayout_2.addWidget(self.windows_long_paths)
         self.verticalLayout_5.addWidget(self.windows_compatibility)
+        self.windows_long_paths = QtWidgets.QCheckBox(RenamingOptionsPage)
+        self.windows_long_paths.setEnabled(False)
+        self.windows_long_paths.setObjectName("windows_long_paths")
+        self.verticalLayout_5.addWidget(self.windows_long_paths)
         self.label_2 = QtWidgets.QLabel(RenamingOptionsPage)
         self.label_2.setObjectName("label_2")
         self.verticalLayout_5.addWidget(self.label_2)
@@ -144,12 +141,22 @@ class Ui_RenamingOptionsPage(object):
         self.verticalLayout_5.addLayout(self.horizontalLayout)
 
         self.retranslateUi(RenamingOptionsPage)
+        self.windows_compatibility.toggled['bool'].connect(self.windows_long_paths.setEnabled) # type: ignore
         QtCore.QMetaObject.connectSlotsByName(RenamingOptionsPage)
         RenamingOptionsPage.setTabOrder(self.move_files, self.move_files_to)
         RenamingOptionsPage.setTabOrder(self.move_files_to, self.move_files_to_browse)
         RenamingOptionsPage.setTabOrder(self.move_files_to_browse, self.move_additional_files)
         RenamingOptionsPage.setTabOrder(self.move_additional_files, self.move_additional_files_pattern)
         RenamingOptionsPage.setTabOrder(self.move_additional_files_pattern, self.delete_empty_dirs)
+        RenamingOptionsPage.setTabOrder(self.delete_empty_dirs, self.rename_files)
+        RenamingOptionsPage.setTabOrder(self.rename_files, self.ascii_filenames)
+        RenamingOptionsPage.setTabOrder(self.ascii_filenames, self.windows_compatibility)
+        RenamingOptionsPage.setTabOrder(self.windows_compatibility, self.windows_long_paths)
+        RenamingOptionsPage.setTabOrder(self.windows_long_paths, self.naming_script_selector)
+        RenamingOptionsPage.setTabOrder(self.naming_script_selector, self.open_script_editor)
+        RenamingOptionsPage.setTabOrder(self.open_script_editor, self.example_filename_before)
+        RenamingOptionsPage.setTabOrder(self.example_filename_before, self.example_filename_sample_files_button)
+        RenamingOptionsPage.setTabOrder(self.example_filename_sample_files_button, self.example_filename_after)
 
     def retranslateUi(self, RenamingOptionsPage):
         _translate = QtCore.QCoreApplication.translate
@@ -160,7 +167,7 @@ class Ui_RenamingOptionsPage(object):
         self.delete_empty_dirs.setText(_("Delete empty directories"))
         self.rename_files.setText(_("Rename files when saving"))
         self.ascii_filenames.setText(_("Replace non-ASCII characters"))
-        self.windows_compatibility.setTitle(_("Windows compatibility"))
+        self.windows_compatibility.setText(_("Windows compatibility"))
         self.windows_long_paths.setText(_("Allow paths longer than 259 characters"))
         self.label_2.setText(_("Selected file naming script:"))
         self.open_script_editor.setText(_("Edit file naming script..."))
diff --git a/ui/options_renaming.ui b/ui/options_renaming.ui
index 1bb2f5e19..57ae43a6b 100644
--- a/ui/options_renaming.ui
+++ b/ui/options_renaming.ui
@@ -19,7 +19,7 @@
     <verstretch>0</verstretch>
    </sizepolicy>
   </property>
-  <layout class="QVBoxLayout" name="verticalLayout_5" stretch="0,0,0,0,0,0,0,0,0">
+  <layout class="QVBoxLayout" name="verticalLayout_5" stretch="0,0,0,0,0,0,0,0,0,0">
    <item>
     <widget class="QGroupBox" name="move_files">
      <property name="title">
@@ -94,25 +94,20 @@
     </widget>
    </item>
    <item>
-    <widget class="QGroupBox" name="windows_compatibility">
-     <property name="title">
+    <widget class="QCheckBox" name="windows_compatibility">
+     <property name="text">
       <string>Windows compatibility</string>
      </property>
-     <property name="checkable">
-      <bool>true</bool>
-     </property>
-     <property name="checked">
+    </widget>
+   </item>
+   <item>
+    <widget class="QCheckBox" name="windows_long_paths">
+     <property name="enabled">
       <bool>false</bool>
      </property>
-     <layout class="QVBoxLayout" name="verticalLayout_2">
-      <item>
-       <widget class="QCheckBox" name="windows_long_paths">
-        <property name="text">
-         <string>Allow paths longer than 259 characters</string>
-        </property>
-       </widget>
-      </item>
-     </layout>
+     <property name="text">
+      <string>Allow paths longer than 259 characters</string>
+     </property>
     </widget>
    </item>
    <item>
@@ -308,6 +303,33 @@
   <tabstop>move_additional_files</tabstop>
   <tabstop>move_additional_files_pattern</tabstop>
   <tabstop>delete_empty_dirs</tabstop>
+  <tabstop>rename_files</tabstop>
+  <tabstop>ascii_filenames</tabstop>
+  <tabstop>windows_compatibility</tabstop>
+  <tabstop>windows_long_paths</tabstop>
+  <tabstop>naming_script_selector</tabstop>
+  <tabstop>open_script_editor</tabstop>
+  <tabstop>example_filename_before</tabstop>
+  <tabstop>example_filename_sample_files_button</tabstop>
+  <tabstop>example_filename_after</tabstop>
  </tabstops>
  <resources/>
+ <connections>
+  <connection>
+   <sender>windows_compatibility</sender>
+   <signal>toggled(bool)</signal>
+   <receiver>windows_long_paths</receiver>
+   <slot>setEnabled(bool)</slot>
+   <hints>
+    <hint type="sourcelabel">
+     <x>226</x>
+     <y>267</y>
+    </hint>
+    <hint type="destinationlabel">
+     <x>226</x>
+     <y>296</y>
+    </hint>
+   </hints>
+  </connection>
+ </connections>
 </ui>