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Agreed. Windows Server 2000 through Windows 7 were peak Microsoft operating system.

By Windows 2000 Server, they finally had the architecture right, and had flushed out most of the 16 bit legacy.

The big win with Windows 7 was that they finally figured out how to make it stop crashing. There were two big fixes. First, the Static Driver Verifier. This verified that kernel drivers couldn't crash the rest of the kernel. First large scale application of proof of correctness technology. Drivers could still fail, but not overwrite other parts of the kernel. This put a huge dent into driver-induced crashes.

Second was a dump classifier. Early machine learning. When the system crashed, a dump was sent to Microsoft. The classifier tried to bring similar dumps together, so one developer got a big collection of similar crashes. When you have hundreds of dumps of the same bug, locating the bug gets much easier.

Between both of those, the Blue Screen of Death mostly disappeared.

You can't say WDDM wasn't a step forward... Being able to crash your video drivers and reboot them without crashing and rebooting your whole machines made Windows a lot more stable.

For folks that pick Windows 2000 Server, why not Server 2003? Is it just because by then NT had XP out as the "Windows for Home Users" and people didn't use Server 2003 as much or were there changes about it folks hated for some reason? To me it always seemed to bring so many more features/capabilities without trashing the classic UI.

It's a shame ReactOS never got mature enough to be a serious competitor. If it had modern app and hidpi support but was suck in a 2000-era UI and didn't have feature bloat, it could be a great daily driver.

Nostalgically, yes, Windows 2000 was amazing. At the time of launch, on period hardware, it was the fastest and most lightweight OS released by Microsoft. And looking back, I always appreciate that I can look in Task Manager and immediately recognize all of the processes by name.

Windows 7 (except for the last few updates that introduced telemetry and ads) comes in as a close second. But everything after is just bloated crapware.

In the 90s, Windows was simple enough that I was able to read tech articles and understand a lot of what is going on inside, up to the point of Windows 2000, and to a certain extend, Windows XP. That completely changed with Vista/7 where I can no longer recognize the name of many processes that are running or understand what actions/situations make my computer lag.

Nowasdays, even through I don't worry anymore as Windows 11 is happy as long as you give it a quadcore cpu, ram, and an SSD, sometimes I still wonder why it writes 40GB to the SSD everyday.

I’ve been running Windows 2000 Pro as my main machine from I think the second beta until it was completely dropped from support.

It ran all of my games, stable as hell, quite light with none of the bullshit added later, none of the graphical bullshit added by XP but still classic Chicago.

The only thing that could make it better were the UI rendering engine introduced with Vista and its enhanced driver and security model.

I started my Windows Server career around 2003R2, so can't comment on the peakness of 2K.

2008R2 snowballed it's own "revolution" when it introduced PowerShell 2.0, which was pivotal for many future things to come.

Out of the more modern ones, 2012R2 was "peak".

I would guess we will still see 2012R2 installations well into the future. Still running bits and pieces of critical infra, even if it has been EOLed long ago, but that's the way of the Server I guess. Can't wait for the 5000+ uptime day screenshots of ancient 2012R2's.

My guess is the next "long LTS" will be Win2025. Just because it's introducing the NTLMv2 deprecation path and working solutions to replace it.

As someone who still runs Win2003 R2 (32bit) on my desktop I can confirm. It was peak MS. System is very stable, UI (classic) is great. It is quick, snappy and good looking. For basic POSIX I have cygwin. For other stuff I use VMs. I have all tools needed to handle some mainmentance (compilers, DDK, docs, ...).

But there is problem.. HW.. The pool of old HW is shrinking, and one day I will not be able to run it anymore.. I guess I will move to Linux. There are few nice and lightweight distros...

Here are my gripes with the modern Windows experience:

- Runs Windows update and reboots without my permission

- Keeps trying to make me switch to Bing

- Keeps trying to make me use Microsoft Account vs. local account

- Does a crappy job of reopening windows on reboot. Miserable copy of macOS.

- Fan spinning on my laptop with no easy way to figure out what process is consuming CPU

- Flat UI

- No built-in way to view markdown files

- No tool to graphically show where my diskspace went; allowing me to find and delete large files

- Printers keep getting disconnected; it is easier to print from iPhone thanks to bonjour

- No dictionary app (macOS has it)

- Can't airdrop to iPhone (3rd party apps can do it)

- No screenshot tool that allows you to type text (in addition to circling and highlighting and arrows)

- No command-line zip / unzip

- No instant search (macOS has had it for how many years now?)

The fact Windows 2000 was peak Microsoft and OS X 10.5 was peak Apple is proof that the golden age of software is way behind us, unfortunately.

Didn't expect to see this-but after Windows 95/98, I went to Windows 2000 for a long time, didn't switch to Windows until 10/11. After Win2k, I went to Linux because I wasn't a fan of XP/7. (I know this is an unpopular take.

Microsoft stopped being the innovator. Now they duplicate or appropriate the innovations of others.

I'm just surprised that it feels like very little deep innovation in the OS world has happened since windows 2k. 3.11 brought networking in. 95 brought true multitasking to the masses and 2k brought multi-processing/multi-user (yes, NT3.1 had it, but 2k is where most normal users jumped in). And, yes, I know these things existed in other OSes out there but I think of these as the mass market kick offs for them. In general I just don't see anything but evolutionary improvements (and back-sliding) in the OS world beyond this time. I had really hoped that true cloud OSes would have become the norm by now (I really want my whole house connected as a seamless collection of stuff) or other major advances like killing filesystems (I think of these as backdoor undocumented APIs). Have we really figured out what an OS is supposed to be or are we just stuck in a rut?

[edit] 3.1 should have been windows for worgkroups 3.11

People just like the Windows they used when they were younger. It's the same with movies, cars, whatever.

Are we just doing OSes or are we doing the entire conglomerate?

#1 Windows 7

#2 DOS 5.0

#3 Office 2003

#4 Windows 95

Honorable mentions: IntelliMouse Optical and XBOX (2001)

As someone who built an IT career on Microsoft’s entire suite, only to recently (past six years or so) migrate wholesale to macOS (endpoint) and Linux (server), I can definitely say MS’ best days are behind it. 2000 was rock solid, Server 2003 had some growing pains (mainly the transition to x64 and multi-core processors), and 2008 fully embraced the long march into irrelevance even as it tried to shake up the hypervisor space. Now the company is so obsessed with arbitrary and unnecessary feature creep and telemetry-as-surveillance that I’m loathe to recommend it when I don’t have to.

Honest to god, if an IdP like Okta made an Active Directory replacement that ran via container instead of a full-fat VM or appliance template, I’d gladly toss ADDS out the window with all its stupid CALs. Basic directory functionality in 2025 shouldn’t require a bloated ADDS/LDAPS virtual machine to run, especially with the move to cloud providers for identity. If you make it easier to do identity without ADDS, you remove Microsof’s major trojan horse into the enterprise - and M365’s as well.

If MS stripped *ALL* ads and bloatware (telemetry for calc??) out of Win 11 and restored the traditional UI of start menu + desktop, it would be fairly good overall. Certainly within their top 5. They really are close to peak yet again but cannot realize they are striving to make it worse.

I see a vast majority of comments here agreeing that UIs were significantly better and faster twenty years ago or more. Assuming HN is representative for the software community, how is it that slow, inferior and dumbed-down interfaces have prevailed in the end? And this hasn't been happening just to popular consumer products.

The glasses are rose-tinted. There were a number of little bits missing from Windows 2000 that were helpful to have in XP, and you could change the theme to make it look just like Windows 2000.

And I really don't know how Windows 7/Server 2008 R2 doesn't win this battle.

For me it's windows 7, if nothing else for being the first and last major Windows where Universal Search worked well.

The Windows 8.x line gets some credit for having the strongest pen interface integration, which regressed significantly in the 10 line, but the overall shell in Windows 8 was rough, and a lot of features were broken in the rushed out and mostly failed attempt to Appify windows and redesign much of the UI at the same time.

Windows 7 was my all-time favorite. I remember you could not use it straight out of the box, there was a whole bunch of UI tweaks that I would make right away. After that, it was perfect.

I think I am not the only one who memorized this: FCKGW-RHQQ2-YXRKT-8TG6W-2B7Q8

the point of an OS is to be out of the way, w2k was both the best and last windows to do so

Let's be real, Windows Server hasn't changed much since W2K... they may have slapped the 7/Vista UI onto it, but at its core, nothing has changed.

It still operates just fine for AD, DHCP, DNS, SMB, etc etc... the only thing they could drop without the majority freaking out is IIS.

2K 100% was the best Windows. The NT benefits with none of the XP downsides.

There are software and scripts to decrapify Windows 11. After uninstalling and stopping everything that's not needed and making start menu and the bar behave like in Windows 7, it's quite decent.

This adds maybe 20 more minutes to install time but it's worth.

Microsoft never should have dropped Xenix to invent its own OS.

You wouldn't want to connect a fresh installation of Windows 2000 to the internet today. "Net Send" and default-on Administrative Shares are some brain-dead design decisions that made sense on a trusted LAN, but not the Internet.

A modern reimagining of Windows 2000's UI - professional, simple, uncluttered, focused, no cheapening of the whole experience with adverts in a thinly-veiled attempt to funnel you into Bing - with modern underpinnings and features such as WSL2 would have me running back towards Microsoft with open arms and cheque book in hand.

I don’t know why they always alternate a good with a bad release. Technically Windows 12 should be good.

That's kinda mean. Surely Windows ME was peak Microsoft.

It felt solid.

It's the Register and therefore too worthless to get worked up about, but their naming a server version of Windows as peak anything is an indication that they probably just polled a few drunks at a bar.

Hard agree. 2000 was capable and never felt bloated.

Windows ME was peak Microsoft, buggy, glitchy, a haven for viruses. It was pure crap and that defined best what Microsoft was and is: cancer

For all I know, windows server 2025 is amazing, but have you priced it out? There's no way to justify it.

I actually like Windows despite their aversion to committing to a UI redesign but do I really need to pay $1100 (per core!?) for the hope (but not the promise) of no ads?

This brings back a lot of nostalgia and I wholeheartedly agree. Back then I ran Windows 2000 server beta 2 on a dual proc system with P2-300s. It was rock solid.

I don't know whether Windows is for corporate desktops, enterprise servers, PC manufacturers, Azure, home users or advertisers. It certainly doesn't feel like it is the right product for me anymore.

The desktop UX was good, but nearly every network service on Windows 2000 had a critical vulnerability at some point. The Code Red worm (MS01-033) comes to mind as particularly impactful. This was the golden age of stack smashing.

I only used Windows at work and I was very happy with NT, when XP came out I was able to go to Linux (RHEL) for my workstation at work.

I never had Windows 2000, but lots of people said it worked great compared to the other Windows systems.

But really for me, the best M/S setup was DOS with Desqview.

Okay, mostly use Windows 7 Professional (with 100+ "updates") for general purpose and software development but for such usage and/or a Web server what to get now? Windows 2xxx?

TBF XP and 7 are both decent. Everything went down after those, including the Ads, the update, etc.

I didn't upgrade to 10 until I purchased a used Dell laptop (which includes 10 prof) a few years ago, and I never used 11 and hopefully never needs to use it.