[menotyou]

Arguably lots of UIs getting worse with every iteration of redesign.

- Windows GUI went downhill from Windows 7 (or even XP) with every release.

- Outlook went from good over fair to annoying so that I finally replaced it as my personal client.

These are not the only examples I could name but they are the most prominent. I think the main problem is that both technical staff and UX designers both trying to make something "new" or "fancy" which is in most cases the opposite of something usable. E.g. Aero was fancy but it took away that my active window had one signal color header bar and all others were tamed. Now all windows are colorful and yelling at me at the same time. Orientation is gone.

And after that UIs got even more "fancy".

Step 13 ("Nobody's happy but nobody hates it") is the plateau when everybody is to tired to keep on fighting - a compromise, not the state of the GUI reached anything acceptable. It is not fancy enough anymore for developers and UX designers to be proud of but at the same time and is still annoyingly bad for the users.

[throwaway2037]

About Outlook: Are you talking about the Win32 desktop client or the M365 web app? If the desktop client, what has gotten so much worse? And is there a better alternative to the Exchange calendar? I have not seen one in my experience at mega corps.