I would say with the release of windows 8.

Vista

Windows 8 with classic shell was fine, I thought.

But most people believed that every other Windows version was good, and hated Windows 8.

Skipping windows 9 is what did them in. Remember when they announced they were skipping 9 and going straight to 10? The writing was on the wall, and plenty of people mention it then.

Media Center was... extra

MS started making bonehead decisions with windows ME, which was an unmitigated disaster. but at least they made some mostly functional and relatively stable OS's after that. but since forcing win11 on everyone and then the constant AI bullshit, it's been nothing but a constant stream of bullshit from them with no end in sight.

they way overestimated the "loyalty" of decades-long users they've been pissing off for years and years. i switched to linux in 2025 after using MS since the 90s, starting with the OG MS-DOS command line

fuck microsoft, fuck windows, and fuck AI

https://m.youtube.com/watch?v=DgJS2tQPGKQ

I feel like it's probably around Windows 8 too, they started tacking on MS store, Xbox, and other stuff nobody wanted. Vista and 7 has also added various telemetry bits, unstable updates, that sort.

Windows 10 was definitely when that accelerated though, forced MS account, sooooo much bloat, etc. And Windows 11 is a disaster for everyone (except the shareholders and data brokers)

They had to skip Windows 9 for technical reasons. A lot of poorly written software was checking the version string and refusing to run because it assumed any version number that started with "Windows 9" was Windows 95 or Windows 98. They didn't skip a whole release cycle, they just changed the version number from 9 to 10.

looks like they doubled down on poorly written software instead

7 was still tolerable. Went to 10 after that and didn't like it, but needed it for gaming.

XP was when

I found Win8 ok but Win8.1 was good since it dialed back the stupid start-screen and under the hood it brought a lot of great functionality for support, management and for power users where it introduced the right click on the start menu for utilities.

It was also fast, I remember at the time it felt snappier than win7 then I saw a video earlier this year comparing all the recent versions vista and higher, and 8.1 came out on top for performance almost across the board

xp's new start menu was bad, at least they still had the old menu as an option until vista. but in 7 they removed that amd forced another menu. and in 8 replaced menu with a screen..

the pre-xp 'classic' menu was nice because you could customize everything

8.1 didn't dial back the start screen, they only added the start button back.

8/8.1 was indeed faster than both 7 and 10. it flies on a core2duo with hdd.

Being old enough to remember Windows not being common, it's always been a mixed bag. It was interesting to see the transition from windows being a thing you sometimes invoked from the commandline to being the thing into which the computer booted. Gamers and others of course had opinions on all those system resources getting used when they weren't even needed.

'98 was stable after some big patches for the most part. XP was really the move to make after that. I used to work tech support and had to learn and support all of the various flavors before XP. I've used XP onward moving as support gets dropped for the previous one, though one of my PCs runs only linux. If davinci would kindly be stable on linux, I would probably switch, maybe keeping windows around for any games I might really want to play.

Hot take, but: shortly after Gates nicked it. ☝🏼

Yep. Fair points all, and I am from the first group: the ones who recall having to type out the code for games in the back of gaming monthlies on pre-Weyland chunky keebs and a green screen. 🤘🏼😅

Everything after Windows NT - after that was when it became more important to be a marketing platform than an actual operating system.

Windows has always been generally bad; I only use it to play video games.

XP was much better compared to 3.1/95/98/Mistake Edition.

I would say it was pretty much a dumpster fire beyond 7, which was okay but Bills "Micro"&"Soft" mostly sold it because if you wanted direct x 12, you had to buy it. The irony was that plenty of developers didn't even use dx12 and/or still supported dx11.

Windows 8...

Windows 10 is interesting. Overall it's now more or less stable. But This is when the downfall became a meteor entering the atmosphere. Things that you didn't ask for, breaking stuff, downloading garbage cr'applications you didn't want or need. Reinstalling them. Forcing updates. Taking away control of your computer. And making just about everything a pain in the fucking ass.

Granted there was some light, LTSB/LTSC were pretty good. But of course what does MicroSlop do? Make it so you can't update your nvidia drivers. (RTX) So yeah not sure if that was entirely on them or some sort of collusion.

And now there's Windows 11. I will never get it. Over the years it's impressive how much of a fuckup that shit is. I don't even have the time to write out how fucked and shit it is.