Indeed looks like it may be breaking some of those tests - they depend on the de-synchronizing state via sending faux keyboard events.
I'm able to repro [the line 2238 failure](https://gitlab.winehq.org/wine/wine/-/blob/d9ad68a1ef1bb9288f5f39199a6042f01...). It happens because of EnterNotify + KeymapNotify pair - the child window is destroyed right before setting up state. This creates the EnterNotify message on the parrent and it's racing with our faux keypreses / key state.
While the tests work on Windows but I believe that this change is still valuable as it creates much better experience for the users and we shouldn't just give up on it. We could get rid of the sync on EnterNotify or change the tests to make sure that the other events are flushed and window state has stabilized before we attempt testing.