Have you seen my MR https://gitlab.winehq.org/wine/wine/-/merge_requests/4406 ? Does it help the original issue as well? I ran your test, and my MR fixes the added todo. Although I get a lot of test failures locally in the existing test (the part of it before your addition) with and without my MR which I suppose are related to some different issues.
If you have some explanation why this change might be better or what did I miss in that MR could you please elaborate if possible?