this post was submitted on 13 Jul 2023
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There has basically been a single "event" in recent memory that a new version of Windows broke compatibility with thousands of games: Windows 10 came with a security patch that broke SafeDisc DRM. Which a tonne of games from the 2000s decade used on their CDs. Ultimately, I don't blame Microsoft. These games were purposely (via a third party) exploiting a security bug in the operating system, and it eventually got fixed.
Apart from that, Microsoft have always (going back to Windows 95) been explicitly supporting backwards compatibility of old software, though obviously there are always exceptions as software uses undocumented features of the OS that break over time.