alt Hacker News> I wonder how much of this problem was caused by lack of adequate documentation describing how an installer should behave, and how much was developers not reading that documentation and being content when it works on their machine.
It was mostly the latter. And when Windows broke, people would blame it on Microsoft, not on the software they installed. The same if the software broke. And you didn’t have online updates at the time that could retroactively add fixes. So Microsoft had to do everything they could to ensure broken software would still work, while also keeping Windows working, the best they could.
> So Microsoft had to do everything they could to ensure broken software would still work
I think they chose to do everything they could to keep it limping along. An alternative would've been a name-and-shame approach, like "This program crashed because the author made this mistake: [short description or code or whatever]", and leave them out to try until the devs stopped doing those dumb things. After a few years of pain, people would've gotten with the program, so to speak. Instead, they chose the path that put zero pressure on devs to write correctly-behaving software.