diff --git a/src/pretix/base/settings.py b/src/pretix/base/settings.py
index 6ff45a5a0..bfa21a658 100644
--- a/src/pretix/base/settings.py
+++ b/src/pretix/base/settings.py
@@ -417,7 +417,7 @@ class SettingsProxy:
         else:
             value = None
             if self._parent:
-                value = self._parent.settings.get(key)
+                value = self._parent.settings.get(key, as_type=str)
             if value is None and key in DEFAULTS:
                 value = DEFAULTS[key]['default']
             if value is None and default is not None:
diff --git a/src/tests/base/test_settings.py b/src/tests/base/test_settings.py
index eff675596..900beb348 100644
--- a/src/tests/base/test_settings.py
+++ b/src/tests/base/test_settings.py
@@ -216,7 +216,7 @@ class SettingsTestCase(TestCase):
         self.assertTrue(f.name.endswith(val.name))
         f.close()
 
-    def test_detect_file_value(self):
+    def test_unserialize_file_value(self):
         val = SimpleUploadedFile("sample_invalid_image.jpg", b"file_content", content_type="image/jpeg")
         default_storage.save(val.name, val)
         val.close()
@@ -227,6 +227,28 @@ class SettingsTestCase(TestCase):
         self.assertTrue(f.name.endswith(val.name))
         f.close()
 
+    def test_autodetect_file_value(self):
+        val = SimpleUploadedFile("sample_invalid_image.jpg", b"file_content", content_type="image/jpeg")
+        default_storage.save(val.name, val)
+        val.close()
+        self.event.settings.set('test', val)
+        self.event.settings._flush()
+        f = self.event.settings.get('test')
+        self.assertIsInstance(f, File)
+        self.assertTrue(f.name.endswith(val.name))
+        f.close()
+
+    def test_autodetect_file_value_of_parent(self):
+        val = SimpleUploadedFile("sample_invalid_image.jpg", b"file_content", content_type="image/jpeg")
+        default_storage.save(val.name, val)
+        val.close()
+        self.organizer.settings.set('test', val)
+        self.organizer.settings._flush()
+        f = self.event.settings.get('test')
+        self.assertIsInstance(f, File)
+        self.assertTrue(f.name.endswith(val.name))
+        f.close()
+
     def _test_serialization(self, val, as_type):
         self.event.settings.set('test', val)
         self.event.settings._flush()