Windows 2000 Server named peak Microsoft. Readers say it's all been downhill since Clippy
- Reference: 1744374550
- News link: https://www.theregister.co.uk/2025/04/11/windows_2000_best_microsoft/
- Source link:
The tech giant is [1]celebrating its 50th birthday , and we [2]asked Register readers for their thoughts on the company's milestones and missteps over the years.
Many of you had a fondness for the halcyon days of Windows NT, with even NT 4 getting a nostalgic nod. However, it was Windows 2000 Server that seemed to attract the most affection.
[3]
Reader Decay remarked: "If I was to formulate a list of requirements and break them into Must Do, Should Do, Like To columns, W2K got the Must Do and Should Do columns nearly all ticked and didn't spend a lot of time in the Like To space."
[4]
[5]
'Bluey agreed, saying: "Sad thing is, back then Windows actually looked like it was going to turn into a great OS. Looked like it was going somewhere."
It was, but not in the direction many of you wanted. Yes, XP and Windows 7 received some love, and even Vista was acceptable for users with suitable hardware (rather than recommended), but Windows 8 and its successors were not universally praised. Windows 8, after all, had a user interface more suited to a mobile device, and Windows 11 has yet to set the world alight.
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Away from desktop Windows, a few readers declared the [7]acquisition of Nokia not necessarily a misstep, but what Microsoft did with Windows Phone thereafter was most definitely a misstep. A lack of an upgrade path for devices, combined with changing development frameworks, left users cold.
[8]No joke: Microsoft foolishly published inaccurate price list on April 1st
[9]Introducing Windows on arm. And by arm, we mean wrist
[10]Windows 11 poised to beat 10, mostly because it has to
[11]Windows intros 365 Link, a black box that does nothing but connect to Microsoft's cloud
One wit ( Boris the Cockroach ) noted that the company's high points were the prices charged for its software, while the low point was the quality of the aforementioned code.
The company's Office productivity suite also received some recognition from readers.
We'd add the company's pivot to the cloud as another of its achievements, if not particularly innovative. Its survival and success despite [12]legal and regulatory challenges to its dominance and [13]sharper business practices is also notable, although unlikely to merit a mention during Microsoft's [14]celebratory event .
Overall, as Microsoft turns 50, the consensus is that the company's best days are receding behind it. Its milestones included the iconic Windows 95, but its early foray into server operating systems is what it is remembered most fondly for.
[15]
It will be up to future IT professionals to decide whether the company's current obsession with AI and its efforts to force the technology on customers will be another notable milestone or something Microsoft will want to forget about in the years to come. ®
Get our [16]Tech Resources
[1] https://news.microsoft.com/microsoft-50/
[2] https://www.theregister.com/2025/04/01/50_years_of_microsoft/
[3] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_software/applications&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=2&c=2Z_k8nQjfcFWOMGyVxsnfPgAAAIs&t=ct%3Dns%26unitnum%3D2%26raptor%3Dcondor%26pos%3Dtop%26test%3D0
[4] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_software/applications&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=4&c=44Z_k8nQjfcFWOMGyVxsnfPgAAAIs&t=ct%3Dns%26unitnum%3D4%26raptor%3Dfalcon%26pos%3Dmid%26test%3D0
[5] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_software/applications&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=3&c=33Z_k8nQjfcFWOMGyVxsnfPgAAAIs&t=ct%3Dns%26unitnum%3D3%26raptor%3Deagle%26pos%3Dmid%26test%3D0
[6] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_software/applications&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=4&c=44Z_k8nQjfcFWOMGyVxsnfPgAAAIs&t=ct%3Dns%26unitnum%3D4%26raptor%3Dfalcon%26pos%3Dmid%26test%3D0
[7] https://www.theregister.com/2024/05/05/microsoft_nokia_anniversary/
[8] https://www.theregister.com/2025/04/07/microsoft_april_1_pricing_mistake/
[9] https://www.theregister.com/2025/04/05/windows_smartwatch_hack/
[10] https://www.theregister.com/2025/04/04/windows_11_market_share/
[11] https://www.theregister.com/2025/04/03/windows_365_link/
[12] https://www.theregister.com/2009/07/25/microsoft_browser_choice_windows_eu/
[13] https://www.theregister.com/2024/12/04/lawsuit_microsoft_windows/
[14] https://news.microsoft.com/microsoft-50/
[15] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_software/applications&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=3&c=33Z_k8nQjfcFWOMGyVxsnfPgAAAIs&t=ct%3Dns%26unitnum%3D3%26raptor%3Deagle%26pos%3Dmid%26test%3D0
[16] https://whitepapers.theregister.com/
From a home-user perspective, Windows 7 remains the best overall OS
I can see how Windows 2000 (server) would have got the most love from the business-oriented users.
Re: From a home-user perspective, Windows 7 remains the best overall OS
Windows 7 isn't the best overall OS. It's 2nd best. 1st best is XP.
XP you could do you anything on it. Stick a DVD in and let it autorun. Great!
Windows 7? You try to do anything with that and all you get is "Are you sure you wanted to install this?". Every time. Every damn time. Fuck off with the nagging already.
Re: From a home-user perspective, Windows 7 remains the best overall OS
I can respect XP as a #1 choice, given its essentially zero telemetry and its hyper-user-focused design. I was an XP holdout until 2015, in fact.
However, Windows 7 did objectively represent an actual upgrade in several significant ways: Practically unlimited RAM support being the biggest upgrade, proper support for SSDs instead of just hard drives, practically unlimited disk partition sizes, and proper implementation of video acceleration at the OS rendering level (Aero theme implementation in particular). Also, I think it's fair to say that the core OS stability of Windows 7 was superior as well. I've run my Windows 7 desktop for the better part of a year without having to reboot or getting a BSOD; I don't think I can say the same for XP.
As for being nagged about "Are you sure you want to install this?" I guess I never really noticed this, given that only install some new program maybe once a month on average.
Re: From a home-user perspective, Windows 7 remains the best overall OS
>However, Windows 7 did objectively represent an actual upgrade in several significant ways:
Agree and that W10, ignoring the telemetry and UI is an under-the-hood functional improvement again on W7.
I suspect if MS had not effectively corrupted the Windows code base when it created W8, it might have been possible to have forked and recreated a W2K look and feel UI/UX with all the under-the-hood functional enhancements of W7 and W10.
>given that only install some new program maybe once a month on average.
Many users probably only install the forced updates to applications installed when they first purchased their system.
Re: From a home-user perspective, Windows 7 remains the best overall OS
AFAICR SP was the first to want to call home to register. That was the star of the slippery slope which has brought Windows users to software by subscription and excessive dependence on somebody else's computer.
Re: From a home-user perspective, Windows 7 remains the best overall OS
I remember W2000 as being reliable, but the start up time was horrendous, at least on the business hardware I was using at the time.
Power on, get coffee, drink coffee, log on.
Microsoft isn't Windows anymore
Sure Bills successors will milk all the money they can from OS sales, but Office365, Teams, Azure (which supports Linux and other OS's on IaaS as well as providing it's own PaaS products) these subscription models are how the firm sees the future. According to SEC filings only 16% of Microsoft income is from Windows.
They have basically given up on desktop computing even as the corporate world firmly has not. Office 365 free works on Firefox or opera on some truly obscure Linux distributions. Yes if you have decades old processes using excel vba macros migrating would be a challenge, and even if you had better alternatives for everything the culture shift would be huge to move a corporations desktop off of windows, but at this point Microsoft isn't the biggest blocker, and would not be materially harmed if it gradually lost the top spot to apple on the desktop, and Linux in the data centre. At some Microsoft acquired outfits in the intel mac era (with macs usually dual booted for windows only stuff) this was the way and the monthly bill to Redmond before acquisition was still massive with office and Azure.
Its a shame because with windows server core and nano, cumulative patches, a willingness to make some of the marmite UI changes optional, and refraining from making peanuts on ads in windows, they could be great even now, and that would be good for Mac/Linux too, the evolutionary pressure would fuel innovation. Its just not a priority as far as I can see.
Re: Microsoft isn't Windows anymore
Their latest dumb terminal that hooks into an Azure desktop is probably the best example of their ignoring the desktop OS
Wonders if they plan on leaving a laptop OS to unix, or do they think everyone will get Chromebooks
Re: Microsoft isn't Windows anymore
It’s been true for a long time that MS makes its reputation on Windows, but its money with Office. (And now, Azure, etc.) This goes back to at least Office 2003. Possibly to 2000. It has been noted on El Reg that Peak MS OS was Windows 2000 Server. This is not a co-incidence.
MS is not alone in having peaked years ago; Peak MacOS was Snow Leopard; starting with Spastic House Cat, err, that is, ‘Lion’, it was a long slide downhill. (Who, me, hate Lion? Whatever gave you that idea?b Just because I was on AppleSeed while Lion was in beta and I spotted and reported several serious problems which were not fixed prior to release. Indeed, some of the problems weren’t fixed until much later; High Sierra for one particularly noxious example. There is one error still listed from Mountain Lion, where they fixed a lot of what was wrong in House Cat, in the little app Apple uses to send in bug reports as not having been fixed. I suspect that it will never be addressed. Every now and again I report it again because it’s till there in current versions of the OS. They’ve stopped acknowledging the reports, not even sending out the infamous ‘working as designed/intended’ reply, possibly because when they send that I reply “This is a piss-poor design and the intent is clearly to annoy users”, but then I have a bad attitude. I suspect “Won’t Fix” is in effect. Bah, humbug. I’ll report it again with the next version of the OS if it’s still there, which it will be.) Peak Linux depends on the distro; Ubuntu is well past its peak, to name one.
Re: Microsoft isn't Windows anymore
"Peak Linux depends on the distro; Ubuntu is well past its peak, to name one."
Anything with systemd is well past its peak. Welcome to the world of ensittification.
Re: Microsoft isn't Windows anymore
"They have basically given up on desktop computing even as the corporate world firmly has not."
I doubt it. It's the teat through which users are expected to suck all those expensive services. What's more, they're not prepared to give it away which is why the 10->11 upgrade is restricted. Those who expect it on old H/W are looking at it from the wrong ange. The only reason it was allowed on recent H/W would have been to block class actions.
Congrats M$
On pulling the wool over so many eyes.
You really should not have existed for this long.
Now please implode.
> what Microsoft did with Windows Phone thereafter was most definitely a misstep. A lack of an upgrade path for devices, combined with changing development frameworks, left users cold.
It was also the developer DRM. You couldn't upload code without a special license from Microsoft. Later, similar was done by Windows RT. It kills passion for early adopters and developers knowing their own code will stop working in the near future.
Windows NT 4.0 Terminal Services is still my favourite to emulate. With rdesktop you can get any resolution you need. NT 4 on a 3440×1440 monitor looks great. So much screen real-estate (the whole purpose for getting a large monitor).
Ah, ya know what?
Big effing yawn.
You people have been dissing Microsoft and Windows since dinosaurs used slate tablets to send neutrino messages to the moon. Frankly, it's gone way past the point of even being boring anymore. It's become SOP, even for people who don't really understand what all the screaming and crying is about. So very sorry that Linux can't manage to become the Desktop of the Year (because as a desktop it stinks); settle for being the server platform of choice, what's wrong with that? As far as I can tell, there are no men in trench coats holding guns to anyone's head and forcing them to use any Microsoft products, especially not the home user happily tootling away on Windows. All the crap I hear about "problems" with Windows is just that--crap. In over 30 years of using Windows I can count the number of actual issues I have had on the fingers on one hand, and of those 5, 3 were due to faulty hardware and the other 2 were 3rd party failures. I haven't seen a BSOD in so long that I've forgotten what they look like.
It became obvious a long while ago that the main thing driving the hatred from the non-Windows people is envy --they cannot stand that their pride and joy, whatever version of Linux or BSD or who-knows-what they use, does not rule the desktop and does not earn the billions of dollars a year that Microsoft does. Golly gosh, Microsoft isn't perfect? Tell me about a corporation, or company, or developer, or Linux package that is perfect, you liar.
Now of course, I'm going to be downvoted into the quicksands of Hades; I knew that when I started typing this little screed but ya know what? I don't care one bit. I don't care if you want to rebut me and tell me how wrong and wrongheaded I am. If I cared, I wouldn't post such mean commentary that doesn't shower admiration on Linux or whatever isn't Windows.
Re: Ah, ya know what?
Your "people complaining about the latest Windows are whiners" tirade might have been valid if we lived in a world where nothing was ever good enough for us, and we were all just complaining about pie-in-the-sky ideas that ought to exist but don't.
But that's not the case. Our pie-in-the-sky ideals have, in fact, already been invented and widely used by a huge portion of the world for many years. Then, those near-perfect implementations have been systematically and forcibly dismantled and replaced over the years by systems that serve the creator rather than the end user, under the guise of "well, you have to use the latest version, it's not safe otherwise".
Re: Ah, ya know what?
"It became obvious a long while ago that the main thing driving the hatred from the non-Windows people is envy--they cannot stand that their pride and joy, whatever version of Linux or BSD or who-knows-what they use, does not rule the desktop and does not earn the billions of dollars a year that Microsoft does."
Completely and utterly arse-about face. The reason many of us prefer Linux or BSD as a desktop is that we're not being bled by corporations earning* billions of dollars a year to produce ever crappier versions of opaque S/W.
We feel a need to genuflect whenever Microsoft pulls out another turkey of a UI. We don't fear every patch Tuesday nor wait ages for updates to download and then reboot and wait for an update to complete. We feel no need to have to submit our PCs to whatever inspection Microsoft demands with the next version of its EULA. We are emphatically not gradually boiled frogs.
* I'm repeating your choice of verb but it is open to dispute.
Re: Ah, ya know what?
I don't give a fuck about the desktop, and nor does M$ any more.
Your criticisms are a straw man, for me at least.
AI obsession
Microsoft's AI obsession will end soon.
Get the popcorn.
"Windows 11 has yet to set the world alight"
The energy demands of all that AI training might yet do so.
Sad but true
I feel that bit barns need both a consumption and heat tax. Yes, I completely understand the impact of that on prices, but if you wish for enterprise to do the right thing, it will be a wasted wish
8.5 years post Windows.
With no regrets whatsoever.
MS can faff around all they like and for people like me, it provides endless entertainment that is also tinged with sadness at all those who have tied their IT life to the MS Mast.
The redmond crew seem to be spending more time fiddling while rome burns recently and ignoring their customers.
I look back at the years I spent fighting the Windows Weirdness and can smile. What is not so funny is their total lack of quality control over their patches.
A long, long time ago, I wrote device drivers for some other operating systems. From time to time, making the changes to the kernel and rebuilding it was a journey into the unknown. The more recent W11 patch releases seem like that.
Windows 2000, now that was when graphics were graphics!