diff --git a/synapse/rest/media/v1/_base.py b/synapse/rest/media/v1/_base.py
index d9c4af9389..c0d2f06855 100644
--- a/synapse/rest/media/v1/_base.py
+++ b/synapse/rest/media/v1/_base.py
@@ -143,6 +143,7 @@ def respond_with_responder(request, responder, media_type, file_size, upload_nam
         respond_404(request)
         return
 
+    logger.debug("Responding to media request with responder %s")
     add_file_headers(request, media_type, file_size, upload_name)
     with responder:
         yield responder.write_to_consumer(request)
diff --git a/synapse/rest/media/v1/media_storage.py b/synapse/rest/media/v1/media_storage.py
index 7f263db239..d23fe10b07 100644
--- a/synapse/rest/media/v1/media_storage.py
+++ b/synapse/rest/media/v1/media_storage.py
@@ -255,7 +255,9 @@ class FileResponder(Responder):
         self.open_file = open_file
 
     def write_to_consumer(self, consumer):
-        return FileSender().beginFileTransfer(self.open_file, consumer)
+        return make_deferred_yieldable(
+            FileSender().beginFileTransfer(self.open_file, consumer)
+        )
 
     def __exit__(self, exc_type, exc_val, exc_tb):
         self.open_file.close()