diff --git a/picard/file.py b/picard/file.py
index b68f62923..b2c59425d 100644
--- a/picard/file.py
+++ b/picard/file.py
@@ -280,7 +280,8 @@ class File(QtCore.QObject, Item):
                 new_filename = self._script_to_filename(format, metadata, settings)
                 if not settings['move_files']:
                     new_filename = os.path.basename(new_filename)
-                new_filename = make_short_filename(new_dirname, new_filename, settings['windows_compatibility'])
+                new_filename = make_short_filename(new_dirname, new_filename,
+                        settings['windows_compatibility'], settings['move_files_ancestor'])
                 # win32 compatibility fixes
                 if settings['windows_compatibility'] or sys.platform == 'win32':
                     new_filename = new_filename.replace('./', '_/').replace('.\\', '_\\')
diff --git a/picard/ui/options/renaming.py b/picard/ui/options/renaming.py
index 73829eedd..62ed6c1be 100644
--- a/picard/ui/options/renaming.py
+++ b/picard/ui/options/renaming.py
@@ -43,6 +43,7 @@ class RenamingOptionsPage(OptionsPage):
         TextOption("setting", "file_naming_format", "$if2(%albumartist%,%artist%)/%album%/$if($gt(%totaldiscs%,1),%discnumber%-,)$num(%tracknumber%,2)$if(%compilation%, %artist% -,) %title%"),
         BoolOption("setting", "move_files", False),
         TextOption("setting", "move_files_to", ""),
+        TextOption("setting", "move_files_ancestor", ""),
         BoolOption("setting", "move_additional_files", False),
         TextOption("setting", "move_additional_files_pattern", "*.jpg *.png"),
         BoolOption("setting", "delete_empty_dirs", True),
@@ -58,6 +59,7 @@ class RenamingOptionsPage(OptionsPage):
         self.ui.rename_files.clicked.connect(self.update_examples)
         self.ui.move_files.clicked.connect(self.update_examples)
         self.ui.move_files_to.editingFinished.connect(self.update_examples)
+        self.ui.move_files_ancestor.editingFinished.connect(self.update_examples)
 
         self.ui.rename_files.stateChanged.connect(self.ui.ascii_filenames.setEnabled)
         self.ui.rename_files.stateChanged.connect(self.ui.file_naming_format.setEnabled)
@@ -65,6 +67,9 @@ class RenamingOptionsPage(OptionsPage):
 
         if not sys.platform == "win32":
             self.ui.rename_files.stateChanged.connect(self.ui.windows_compatibility.setEnabled)
+            self.ui.rename_files.stateChanged.connect(self.toggle_move_files_ancestor_enabled)
+            self.ui.windows_compatibility.stateChanged.connect(self.toggle_move_files_ancestor_enabled)
+            self.ui.move_files.stateChanged.connect(self.toggle_move_files_ancestor_enabled)
 
         self.ui.move_files.stateChanged.connect(self.ui.delete_empty_dirs.setEnabled)
         self.ui.move_files.stateChanged.connect(self.ui.move_files_to.setEnabled)
@@ -75,6 +80,16 @@ class RenamingOptionsPage(OptionsPage):
         self.ui.file_naming_format_default.clicked.connect(self.set_file_naming_format_default)
         self.highlighter = TaggerScriptSyntaxHighlighter(self.ui.file_naming_format.document())
         self.ui.move_files_to_browse.clicked.connect(self.move_files_to_browse)
+        self.ui.move_files_ancestor_browse.clicked.connect(self.move_files_ancestor_browse)
+
+    def toggle_move_files_ancestor_enabled(self):
+        enabled = self.ui.rename_files.isChecked() and \
+                  self.ui.windows_compatibility.isChecked() and \
+                  self.ui.windows_compatibility.isEnabled() and \
+                  self.ui.move_files.isChecked()
+        parentLayout = self.ui.move_files_ancestorLayout
+        for i in range(parentLayout.count()):
+            parentLayout.itemAt(i).widget().setEnabled(enabled)
 
     def check_formats(self):
         self.test()
@@ -88,7 +103,8 @@ class RenamingOptionsPage(OptionsPage):
             'move_files': self.ui.move_files.isChecked(),
             'use_va_format': False, # TODO remove
             'file_naming_format': unicode(self.ui.file_naming_format.toPlainText()),
-            'move_files_to': os.path.normpath(unicode(self.ui.move_files_to.text()))
+            'move_files_to': os.path.normpath(unicode(self.ui.move_files_to.text())),
+            'move_files_ancestor': unicode(self.ui.move_files_ancestor.text())
         }
         try:
             if self.config.setting["enable_tagger_script"]:
@@ -123,6 +139,8 @@ class RenamingOptionsPage(OptionsPage):
         self.ui.file_naming_format.setPlainText(self.config.setting["file_naming_format"])
         self.ui.move_files_to.setText(self.config.setting["move_files_to"])
         self.ui.move_files_to.setCursorPosition(0)
+        self.ui.move_files_ancestor.setText(self.config.setting["move_files_ancestor"])
+        self.ui.move_files_ancestor.setCursorPosition(0)
         self.ui.move_additional_files.setChecked(self.config.setting["move_additional_files"])
         self.ui.move_additional_files_pattern.setText(self.config.setting["move_additional_files_pattern"])
         self.ui.delete_empty_dirs.setChecked(self.config.setting["delete_empty_dirs"])
@@ -130,8 +148,21 @@ class RenamingOptionsPage(OptionsPage):
 
     def check(self):
         self.check_format()
-        if self.ui.move_files.isChecked() and not unicode(self.ui.move_files_to.text()).strip():
-            raise OptionsCheckError(_("Error"), _("The location to move files to must not be empty."))
+        if self.ui.move_files.isChecked():
+            move_files_to = unicode(self.ui.move_files_to.text()).strip()
+            if not move_files_to:
+                raise OptionsCheckError(_("Error"), _("The location to move files to must not be empty."))
+            if self.ui.windows_compatibility.isChecked() and self.ui.windows_compatibility.isEnabled():
+                move_files_ancestor = unicode(self.ui.move_files_ancestor.text()).strip()
+                if move_files_ancestor:
+                    move_files_to = os.path.abspath(move_files_to)
+                    move_files_ancestor = os.path.abspath(move_files_ancestor)
+                    if not move_files_to.startswith(move_files_ancestor) or \
+                            move_files_to.split(move_files_ancestor)[1][:1] not in (os.path.sep, ""):
+                        raise OptionsCheckError(
+                            _("Error"),
+                            _("Compatibility must be applied against an ancestor of where files are moved to.")
+                        )
 
     def check_format(self):
         parser = ScriptParser()
@@ -151,6 +182,7 @@ class RenamingOptionsPage(OptionsPage):
         self.tagger.window.enable_renaming_action.setChecked(self.config.setting["rename_files"])
         self.config.setting["move_files"] = self.ui.move_files.isChecked()
         self.config.setting["move_files_to"] = os.path.normpath(unicode(self.ui.move_files_to.text()))
+        self.config.setting["move_files_ancestor"] = unicode(self.ui.move_files_ancestor.text())
         self.config.setting["move_additional_files"] = self.ui.move_additional_files.isChecked()
         self.config.setting["move_additional_files_pattern"] = unicode(self.ui.move_additional_files_pattern.text())
         self.config.setting["delete_empty_dirs"] = self.ui.delete_empty_dirs.isChecked()
@@ -220,6 +252,12 @@ class RenamingOptionsPage(OptionsPage):
             path = os.path.normpath(unicode(path))
             self.ui.move_files_to.setText(path)
 
+    def move_files_ancestor_browse(self):
+        path = QtGui.QFileDialog.getExistingDirectory(self, "", self.ui.move_files_ancestor.text())
+        if path:
+            path = os.path.normpath(unicode(path))
+            self.ui.move_files_ancestor.setText(path)
+
     def test(self):
         self.ui.renaming_error.setStyleSheet("");
         self.ui.renaming_error.setText("")
diff --git a/ui/options_renaming.ui b/ui/options_renaming.ui
index 8e05f07ec..7131be922 100644
--- a/ui/options_renaming.ui
+++ b/ui/options_renaming.ui
@@ -72,6 +72,43 @@
      </item>
     </layout>
    </item>
+   <item>
+    <layout class="QHBoxLayout" name="move_files_ancestorLayout">
+     <property name="spacing">
+      <number>2</number>
+     </property>
+     <item>
+      <widget class="QLabel" name="move_files_ancestor_label">
+       <property name="enabled">
+        <bool>false</bool>
+       </property>
+       <property name="text">
+        <string>Apply compatibility against:</string>
+       </property>
+      </widget>
+     </item>
+     <item>
+      <widget class="QLineEdit" name="move_files_ancestor">
+       <property name="enabled">
+        <bool>false</bool>
+       </property>
+       <property name="text">
+        <string/>
+       </property>
+      </widget>
+     </item>
+     <item>
+      <widget class="QPushButton" name="move_files_ancestor_browse">
+       <property name="enabled">
+        <bool>false</bool>
+       </property>
+       <property name="text">
+        <string>Browse...</string>
+       </property>
+      </widget>
+     </item>
+    </layout>
+   </item>
    <item>
     <widget class="QCheckBox" name="delete_empty_dirs">
      <property name="enabled">