Windows 2000 was the peak - rock solid with no visual fluff. XP was 2000 with a childish skin on it and it’s all downhill from there.

It’s all been downhill since Windows 7. All versions of windows after 7 are just windows 7 with extra bloatware, garbage and Ads.

Windows 7. Some may say 8.1 if they were willing to tolerate it, but most will agree that Win7 was the last “true” OS that wasn’t riddled with adware and telemetry collection.

Microsoft lost a lot of money on Win8 (and by extension, 8.1). That made them rethink their business model, and they shifted away from selling the OS. Instead, they gave the OS away and made money on the data collection. Because Win8 made them realize that the world didn’t want or need a new OS every other year.

It’s the same reason people don’t upgrade their cell phones every year anymore. At first, the hardware changes were meaningful, and you actually got large upgrades with every new iteration. You were noticeably behind if you had a phone that was two or three years old. But now that modern hardware design has slowed down, (and hardware changes are more akin to updates on existing hardware), people don’t feel like they’re behind if they put off upgrading for two or three years.

And this reluctance to upgrade hardware meant people and businesses weren’t constantly buying a new OS every year. So Microsoft lost a lot of money when Win8 launched and everyone collectively went “actually, I’m good with my current computer.”

I’m going to say Win8 & 8.1.

Say what you will about the UI, they did great work on the underlying kernel, file system and APIs. If they’d continued to refine it, it’d be damn near perfect.

They really started to lose the plot with 10; it kept a lot of what made 8 good (and steals a lot of goodwill from 8) but you can see the adware and telemetry start to creep in.

The next best I’d have to give to Vista, which also did some much needed revitalization, only to see 7 get the glory because Microsoft flubbed the hardware requirements and vendors were sloppy with drivers.

My favourite is NT3.5: full microkernel, no GDI in kernel space, no printer drivers in the kernel, less registry issues. We’d have skipped a lot of pain from the 90s and 2000s had Microsoft not went backwards with 9x and NT4.

Its been a gradual decline over many years. I’d say the tipping point was Microsoft Edge or Windows 10 itself - that’s around the time the explicit attempts to “monetise” users started.

When Windows went “free” the focus became how to extract as much money per user all the time, so the advertising and edge based spying / data harvesting stepped up a gear.

Its not a surprise looking back - the drive for all these companies with stock holders is “growth”. That really means growth in the share price which means growth in revenue or profits amongst other tricks. Everytime a new generation of managers comes through they scrape the barrel for ideas and things get worse and worse.

I only use windows at work now; I’ve migrated all my devices to Linux (desktpp, laptop, media PC)

Their objectives went south around windows 8.

They screwed up execution before, certainly, and in never was a huge fan, but they were at least trying to make what they sincerely thought was a intrinsically good desktop experience until 8.

Windows 8 was when they had the fear of Android and iOS and the Microsoft phone os was failing on its own, so the mission for Windows 8 was to throw the desktop user experience under the bus for the sake of trying to bolster the phone platform, and maybe make PCs that were tablet like. Also seeing Apple and Google succeed with Internet account based access to the devices was a motivation to get people into an online ecosystem that would have the way to indefinite monthly payments and an app store where they could take a cut off all the application vendors’ revenue.

I think there are two eras that have some overlap:

1. Microsoft developed new versions of Windows to be more compelling by adding features, capabilities, new hardware compatibility, etc. I think this was the main era they were in from the inception of Windows to somewehere in the XP-Vista-7 era, and fully ended a couple years into Win 10.

2. Microsoft developed new versions of Windows mainly as spyware to extract data from and about users to exploit themselves or sell to other parties. I believe this started late in the Win 7 era and really took off mid-Win 10 and is continuing to escalate.

Note: I don’t think they ever really cared about their users needs or wants, because their main business strategy has always been elimination of competition as much as the law would allow. No one asked for the caramel pepperoni milkshake that was Win 8’s half desktop half tablet UI, they incorrectly thought they could horn in on the iPad market if they half assed it just enough. Most of Win 10’s history has been “Microsoft is going all in on [trendy bullshit]!” 6 months later “Microsoft is ripping out all support for [trendy bullshit].” Their inferior voice assistant, 3D, AR, AI, all this stupid crap no one wants. Microsoft’s attempts at anticipating what users want in a computer platform began and ended with Microsoft Bob.

Windows 10 was initially developed to stop the very negative reaction to Windows 8. Around that time, it became clear to Microsoft that they weren’t going to profit on Windows itself any more and the future was in the cloud.

Windows did a lot of underhanded things to keep people updating Windows and Office before, but it wasn’t trying to sell services as a way to keep the company up and running.

The correct answer is “whenever you discovered there was an alternative”. Windows has always been shit, but before you thought there was no alternative so you were used to it, ever since you started using something different you’ve grown less tolerant of problems. It’s like someone who’s always had a low end PC and played games on minimum at 30fps, it’s “okay” but the moment you play something on maximum at 144fps your normal experience feels sluggish and bad (even though nothing really changed with it).

I think windows is the same thing, which is why most people will tell you the last good version of windows was the one they were using when they migrated over to Linux.

Microsoft has always made windows good… … … For them.

When it became more profitable for them to develop it to be shit

Windows 2000 (Windows NT 5.0) was the last great version of windows. It was fucking fantastic.

I’ve also heard great things about Windows server 2008, but I had departed from the entire Microsoft sphere years before that.

*nix4Lyf!

There’s not much competition, they can’t make more money to increase shareholder value by improving the product because they pretty much have all the marketshare they need.

The only way to make more money is by monetizing your data and selling you more and more ads. Which they will do more and more year after year since they need to increase profits year after year for shareholders.

Windows 7 was the last one. Windows 10 is usable, but it was created with advertising in mind.

Vista

I dunno, but it might have something to do with external factors. Like, once upon a time Microsoft was sued by the US government under anti-trust laws for bundling a web browser in their operating system. Now MS force their users to experience unavoidable advertising when they try to use their own computers, and there’s not a peep from regulators.