diff --git a/synapse/rest/media/v1/_base.py b/synapse/rest/media/v1/_base.py
index b9600f216..bce077bec 100644
--- a/synapse/rest/media/v1/_base.py
+++ b/synapse/rest/media/v1/_base.py
@@ -17,6 +17,7 @@ from synapse.http.server import respond_with_json, finish_request
 from synapse.api.errors import (
     cs_error, Codes, SynapseError
 )
+from synapse.util import logcontext
 
 from twisted.internet import defer
 from twisted.protocols.basic import FileSender
@@ -103,7 +104,9 @@ def respond_with_file(request, media_type, file_path,
         )
 
         with open(file_path, "rb") as f:
-            yield FileSender().beginFileTransfer(f, request)
+            yield logcontext.make_deferred_yieldable(
+                FileSender().beginFileTransfer(f, request)
+            )
 
         finish_request(request)
     else: