diff --git a/bridgev2/matrix/intent.go b/bridgev2/matrix/intent.go
index 3d2692f9..173f7c15 100644
--- a/bridgev2/matrix/intent.go
+++ b/bridgev2/matrix/intent.go
@@ -403,6 +403,7 @@ func (as *ASIntent) UploadMediaStream(
 			removeAndClose(replFile)
 			removeAndClose(tempFile)
 		}
+		req.AsyncContext = zerolog.Ctx(ctx).WithContext(as.Connector.Bridge.BackgroundCtx)
 		startedAsyncUpload = true
 		var resp *mautrix.RespCreateMXC
 		resp, err = as.Matrix.UploadAsync(ctx, req)
@@ -435,6 +436,7 @@ func (as *ASIntent) doUploadReq(ctx context.Context, file *event.EncryptedFileIn
 				as.Connector.uploadSema.Release(int64(len(req.ContentBytes)))
 			}
 		}
+		req.AsyncContext = zerolog.Ctx(ctx).WithContext(as.Connector.Bridge.BackgroundCtx)
 		var resp *mautrix.RespCreateMXC
 		resp, err = as.Matrix.UploadAsync(ctx, req)
 		if resp != nil {
diff --git a/client.go b/client.go
index 3aa1627d..2503556a 100644
--- a/client.go
+++ b/client.go
@@ -1933,10 +1933,15 @@ func (cli *Client) UploadAsync(ctx context.Context, req ReqUploadMedia) (*RespCr
 	}
 	req.MXC = resp.ContentURI
 	req.UnstableUploadURL = resp.UnstableUploadURL
+	if req.AsyncContext == nil {
+		req.AsyncContext = cli.cliOrContextLog(ctx).WithContext(context.Background())
+	}
 	go func() {
-		_, err = cli.UploadMedia(ctx, req)
+		_, err = cli.UploadMedia(req.AsyncContext, req)
 		if err != nil {
-			cli.Log.Error().Stringer("mxc", req.MXC).Err(err).Msg("Async upload of media failed")
+			zerolog.Ctx(req.AsyncContext).Err(err).
+				Stringer("mxc", req.MXC).
+				Msg("Async upload of media failed")
 		}
 	}()
 	return resp, nil
@@ -1972,6 +1977,7 @@ type ReqUploadMedia struct {
 	ContentType   string
 	FileName      string
 
+	AsyncContext context.Context
 	DoneCallback func()
 
 	// MXC specifies an existing MXC URI which doesn't have content yet to upload into.