They still do. I have Win95 games that were broken in WinXP but started working in Win7 x64, or ones that broke in Win7 x64 and started working again in Win10.

I'm having the opposite experience, I tried playing an old DirectX 9 game the other day and it was unplayable in Windows. It did at least boot and menus worked fine, but for some reason for another the framerate in-game was so low it was unplayable. A few days later I tried it on my linux machine with Wine and it was perfect (thank god for DXVK).

dgVoodoo is great for old DirectX games: http://dege.freeweb.hu/

thats not true, plenty of games needed win 10 support. like blizzard games (diablo (2), warcraft (3), etc.) and many others even age of empires 1/2 needed to support windows 10 via patches and did not work out of the box.

It definitely varies by game, but that's always been the case. One of the games I mentioned was broken by XP but fixed by Windows 7.

"Works for me (TM)"

Windows Desktop Evangelism playbook hasn't changed since 2000.

The Windows 2000 / ME debacle appeared to be the breaking point when Microsoft realized they needed to adopt a more Apple-like approach to evolving the platform.

Perfect backwards compatibility means a perfect inability to fix any mistakes of the past.

With UAC and WDM -> WDF, they finally established an intent to deprecate older (and insecure / poorly-designed) functionality.

That said, imho, the user-mode / UI/X compatibility is an absolute !*&$ show with respect to predictability. Especially in the "utility program -> app" transition, wherein the latter still aren't feature-complete. Whoever PMs over those teams should be fired.

By curious coincidence, Windows just threw me this: https://i.imgur.com/iUWoHOw.png

It's disabled the VirtualBox install that I've been running for a year or so with no issues, on the basis that it's "old software".

This certainly shows the true face of the new Microsoft.