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I don't think the XP->Vista upgrade is a good example for the argument you make. Vista is ubiquitously considered a failure and disaster. Its adoption was slow and many who adopted early were disappointed, even though microsoft was running ad campaigns to get people to upgrade. People started upgrading only after windows 7.

Similarly, windows 8 failed to get traction. Most people upgraded with windows 10 (and prob a lot of them due to eol fears).

Should we also mention windows 2000? There is definitely sth with microsoft failing completely every 2 OS generations since then. Maybe they need the feedback to make sth that people wanted to use.

I am less optimistic about the future, though, because I doubt they will double down on bloatware and monetising users, too much money at stake.






Windows 2000 was pretty good, though? Basically XP with the old Windows 9x UI.

MS just decided primarily target Millennium to consumers which wasn’t that great..




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