diff --git a/mopidy/utils/settings.py b/mopidy/utils/settings.py
index 6286c8b9..3145d278 100644
--- a/mopidy/utils/settings.py
+++ b/mopidy/utils/settings.py
@@ -51,7 +51,7 @@ class SettingsProxy(object):
         value = self.current[attr]
         if type(value) != bool and not value:
             raise SettingsError(u'Setting "%s" is empty.' % attr)
-        if attr.endswith('_PATH'):
+        if attr.endswith('_PATH') or attr.endswith('_FILE'):
             value = os.path.expanduser(value)
             value = os.path.abspath(value)
         return value
diff --git a/tests/utils/settings_test.py b/tests/utils/settings_test.py
index 3b1d7439..cef0069d 100644
--- a/tests/utils/settings_test.py
+++ b/tests/utils/settings_test.py
@@ -73,12 +73,30 @@ class SettingsProxyTest(unittest.TestCase):
         expected = os.path.expanduser('~/test')
         self.assertEqual(acctual, expected)
 
-    def test_value_not_ending_in_path_is_not_expanded(self):
+    def test_value_ending_in_path_is_absolute(self):
+        self.settings.TEST_PATH = './test'
+        acctual = self.settings.TEST_PATH
+        expected = os.path.abspath('./test')
+        self.assertEqual(acctual, expected)
+
+    def test_value_ending_in_file_is_expanded(self):
+        self.settings.TEST_FILE = '~/test'
+        acctual = self.settings.TEST_FILE
+        expected = os.path.expanduser('~/test')
+        self.assertEqual(acctual, expected)
+
+    def test_value_ending_in_file_is_absolute(self):
+        self.settings.TEST_FILE = './test'
+        acctual = self.settings.TEST_FILE
+        expected = os.path.abspath('./test')
+        self.assertEqual(acctual, expected)
+
+    def test_value_not_ending_in_path_or_file_is_not_expanded(self):
         self.settings.TEST = '~/test'
         acctual = self.settings.TEST
         self.assertEqual(acctual, '~/test')
 
-    def test_value_not_ending_in_path_is_not_absolute(self):
+    def test_value_not_ending_in_path_or_file_is_not_absolute(self):
         self.settings.TEST = './test'
         acctual = self.settings.TEST
         self.assertEqual(acctual, './test')