diff --git a/changelog.d/19062.bugfix b/changelog.d/19062.bugfix
new file mode 100644
index 00000000000..c5231cbbc8c
--- /dev/null
+++ b/changelog.d/19062.bugfix
@@ -0,0 +1 @@
+Fix a bug introduced in 1.111.0 where failed attempts to download authenticated remote media would not be handled correctly.
\ No newline at end of file
diff --git a/synapse/http/matrixfederationclient.py b/synapse/http/matrixfederationclient.py
index 15f8e147ab6..60684bc48ec 100644
--- a/synapse/http/matrixfederationclient.py
+++ b/synapse/http/matrixfederationclient.py
@@ -1719,6 +1719,7 @@ async def federation_get_file(
                     response, output_stream, boundary, expected_size + 1
                 )
                 deferred.addTimeout(self.default_timeout_seconds, self.reactor)
+                multipart_response = await make_deferred_yieldable(deferred)
         except BodyExceededMaxSize:
             msg = "Requested file is too large > %r bytes" % (expected_size,)
             logger.warning(
@@ -1755,7 +1756,6 @@ async def federation_get_file(
             )
             raise
 
-        multipart_response = await make_deferred_yieldable(deferred)
         if not multipart_response.url:
             assert multipart_response.length is not None
             length = multipart_response.length