Recently I had need to reinstall Windows 2000 Professional, which I did in a Virtual Machine (I used VMWare's Workstation Player, which is free for non-commercial use). Now, although my usage of Win2K Pro was itself going to be relatively restricted and I had installed a version that came with Service Pack 4, I decided it'd probably be best if I did update it, but when I ran Windows Update I unsurprisingly found it just didn't work. It wasn't surprising because of how old the OS is now and also because its extended support period ended almost ten years ago. I did find out though that it is possible to fix, which was surprising.
There's a lot of misinformation out there about how to actually get it working again, mostly because it appears lots of people that explain how to do it did so years ago when perhaps certain software requirements were different and various websites still existed. After a bit of trial and error though I did figure out how to get it working by myself and it's not all that difficult either, all you may have trouble with is obtaining one or two of the files you need as old resources pointing to them either don't exist or are outdated. Anyway without further ado, you need the following files and to install them in this order:
- Service Pack 4
- Microsoft Internet Explorer 6 Service Pack 1 (Windows 2000)
- Root Certificates Update
- Microsoft Windows Installer 3.1
- Update for Background Intelligent Transfer Service (BITS) 2.0 and WinHTTP 5.1 (KB842773)
- Windows Update Agent
- Enable "Use TLS 1.0" in Internet Options
Firstly telling you to install SP4 is a given, but I highly recommend you install 2K Pro from a source that already includes it for the sake of ease, I only mention the service pack in case you forgot and are installing Windows from an older source that didn't include it. Secondly the Root Certificates Update is a silent install; once you run it nothing will appear to happen but it has in fact installed as expected in the background. Thirdly I'm not entirely sure if it's necessary to install Windows Update 3.1 for this process but even if it isn't you might as well update it while you're at it. Lastly that 'Use TLS 1.0' option you need to change is fairly simple to do; it's located under the security heading on the advanced tab of the Internet Options control panel:
You may have already discovered to your annoyance that I haven't actually linked to any direct downloads but have instead linked to pages that have links to the downloads. The 3rd and 5th links simply point to search results in the Microsoft Update Catalogue website, which is not particularly helpful on my part I know and I apologise if that's pissed you off, but I am unsure of Microsoft's hotlinking policy for the catalogue website and besides which it seems a bit buggy and somewhat dynamic in the way it generates results, so direct linking probably wouldn't work anyway.
If you click one of these two links, it will direct you to the website with a search query in place to bring up results that hopefully include the ones you need to download. However this website has a frequent tendency to do one of three things; either show you the result you need in amongst a bunch of other results that you don't, show you a bunch a results that do not include the result you need even though it should (see picture below), or just not show you anything at all.
It's clearly a bit beta in nature, or just badly coded. Either way what you want to do when searching the catalogue is to make sure the update listed has "Windows 2000" in the Products field (bare in mind some updates apply to more than one Windows OS too). If you search for an update and it brings up results for other operating systems but not for Windows 2000 (common for the BITS update as shown above), keep refreshing the page or clicking the search button on the top right and eventually it'll show you the update you're actually looking for… Well it should do anyway. While refreshing the page two or three times usually gets it to work, I have found on occasions that I had to wait a while before searching again so it would list the updates I wanted.
That's not the end of it though, as once you click on the download button for an update it'll open a new window with the actual links to the files. There's usually one or two, but sometimes several (oft for different languages if the update needed to be localised). However even this doesn't always work properly and you may get weird file links or an error, but again reloading it usually works and this may be required several times. It's less glitchy than the search function though so it does seem to work as expected most of the time. However for the sake of making things easier for you, once you've downloaded the files you can compare them to this list of filenames to make sure you got the right ones:
On the positive side though, it does seem Microsoft have almost every update they ever released for older operating systems on this catalogue website, so if you for instance wanted to download every update for Windows 2000 Pro yourself and store them somewhere for safe keeping you can for the most part. If however you run into trouble and cannot find anything on the catalogue, the Internet Archive does tend to have pages from Microsoft's old download websites and even the files saved, but I'll leave that up to you to figure out.