diff --git a/src/components/structures/RoomView.tsx b/src/components/structures/RoomView.tsx
index f568f31dbd..4c418e9994 100644
--- a/src/components/structures/RoomView.tsx
+++ b/src/components/structures/RoomView.tsx
@@ -672,9 +672,10 @@ export default class RoomView extends React.Component<IProps, IState> {
                     handled = true;
                 }
                 break;
+            case Key.U: // Mac returns lowercase
             case Key.U.toUpperCase():
                 if (isOnlyCtrlOrCmdIgnoreShiftKeyEvent(ev) && ev.shiftKey) {
-                    dis.dispatch({ action: "upload_file" });
+                    dis.dispatch({ action: "upload_file" }, true);
                     handled = true;
                 }
                 break;