Raymond Chen wrote some articles about how this impacted Windows 95. It doesn't matter that program X completely ignored the documentation in Windows 3.x and so it "makes sense" technically that in Win95 that program crashes, the user experience is that Windows 95 broke Program X, and they just bought Windows 95, so they will demand a refund and moan to all their friends.
There is a limited tolerance for Chrome versions that don't work, because the lesson customers get is "Don't run Chrome" not "My middlebox is garbage". The tolerance is increased for security problems, so Google is more willing to lose say 0.1% of users because they enabled TLS 1.3 (the remaining 99.9% of users get improved security) than to lose 0.1% of users because they added a cool 3D logo and it crashes on a specific model of video card or version of Windows due to a driver bug. But losing 10% of your users is a disaster, and that was the ballpark for TLS 1.3 in earlier drafts (before it was taught to sidestep more middleboxes).