My former employer had to stick with Windows 2000 to support an oddball application that introduced some disagreeable licensing terms in the XP\2003 supporting version and quite frankly it has only been recently that they have run into tangible problems with supporting Windows 2000 as Firefox has dropped support and Sophos Endpoint became unstable. I don't see XP becoming wholly unserviceable anytime soon.

I agree with all of the above. IMHO there are several things to consider regarding when to retire these XP machines:

As previously mentioned, Microsoft XP SP3 support will end in April 2014. Of course this doesn't mean that the OS will stop working, but it does mean MS will stop creating, testing, and releasing security updates for the OS.

Microsoft terminated all support for Office 2000 in June 2009. Support for Office 2003, including security update support, will end in April 2014.

You can expect 3rd-party software applications to discontinue development and patch support for XP next April (some have done so already.) That means you may need to continue using your current version of web browser, PDF reader, Java, etc. without access to updates. This may introduce problems with release of future technology integrated with new applications (e.g. HTML5 etc.) It's also possible that your antivirus and/or malware applications won't continue to receive updates compatible with XP.

Most new devices already are delivered with drivers and other software compatible with mainstream OS which are currently sold and supported by Microsoft. If you think you may need a new printer before you replace those XP machines, you should probably consider buying one soon.

I don't think the bad guys will increase efforts to target new malware aimed at OS that are fading into the sunset. But I do think that some new malware aimed at newer OS may affect older OS too. MS will continue effort to create security patches for the newer OS, but not for XP, Office 2000, or Office 2003.

Since the OP doesn't seem to be experiencing any of these issues now, and is content with XP, I see no reason to change now. But the end is near.

Hmmm. Just had a situation that made me wonder.

My RAID server is in a smallish case in the basement. I noticed that the power switch had broken, and a couple of other minor annoyances. So, I decided to put in in a larger case. More room to "breathe", more fans, etc. After all, it runs 24/7.

So, I moved everything over, and when I started it up I got the "Your hardware has significantly changed ... you have 3 days to activate Windows" message. Never saw that before, but I finished and then went to activate it, which it did in a matter of seconds. Fine. But ...

What if some time in the future I run into a similar problem? Or I have to do a recovery install? Or a whole clean install? If Microsoft is no longer supporting the OS, will I be able to activate it? What's their history been on no-longer supported products that you have to have them activate?

That's one sure way to get people to spring for an upgrade.

Magic 8 Ball says "Signs point to yes".

Even though MS is ending support for XP next year, they've extended XP downgrade rights for Windows 7 Pro & Ultimate customers throughout the Windows 7 support lifecycle. That means XP activation functionality needs to remain in place through 2020. More info at this link.

Thank you! Great links!

By 2020, I might very well be pushing up daisies, so I guess I can sleep easier for a few more years.

Office 2000 had a kill switch for Product Activation and it was disabled in April of 2003. Presumably they can do the same with XP.

Adobe, which lacked a kill switch, released a de-DRMed version of CS2, and then went "oops!" when people realized that was basically a free-for-all to download without a license.

Is CS2 even usable on a modern Mac or PC?

No idea about Macs, but the last time I checked it ran fine on Windows 7 64-bit relatively fine; IIRC, it generated some UAC warnings you had to click through the first time you actually ran the app, and otherwise ran without problem.

It's also, last I checked, the latest version that runs usefully in WINE on Linux.

If you avoid 'dodgy' sites then I don't think security will be your issue. I think it will be the lack of support for 3rd party apps.

I use Win8 for work and home. I know that upgrading a pc's is an annoying task so you might as well skip over 7 and just upgrade to 8 now.

Man, I love Win2k. I still use it occasionally in a virtual machine, and it recently allowed me to recover some files saved in Works back in, oh, 1994 or so.

That said, I don't let it on the Net because I don't know what vulnerabilities exist. Running most (many? all?) modern anti-virus programs is out of the question because they are incompatible. WinXP will be in the same boat someday, so that's something to keep in mind. Having a good, strict firewall set up is an option to consider, and it doesn't have to be expensive. Editing your Hosts file is another _very_ good layer of security, but explaining that is outside the scope of this article.

If XP does what you want, go ahead. The main thing is don't use IE, as that won't get any security fixes. Firefox, Opera, and Chrome will still work and still get updates for the immediate future.

I never had to re-install XP as much as earlier versions of Windows, but did have problems occasionally, almost always after installing a new program. If you aren't installing new software, this probably won't be a problem. The installation process in XP is still pretty fragile.

I've had the old hardware problem myself. A business I worked at in 1999 was still running an old PS/2 running DOS because it had a special Microchannel interface card to work with a 9 track tape drive. They funded the replacement PCI card (multiple thousands of dollars) with the Y2K remediation budget.

I've installed Office 2000 on several machines. There is no on-line activation; just enter the Product ID that came with the CD and off you go.

As of now, Win7 is as far as I'm willing to go. The jury is still out on Win8, at least for the type of computer usage I do.

My hosts file went from 768 bytes to about 600K. A quick Google search will turn up several sites where complete files can be found for free.

I use IE6, which comes with SP3, and immediately upgrade it to IE8, which is far as you can go with XP. That at least gets me to most sites. After that, Chrome seems to do the job fine. As you say, upgrades/fixes are more likely with Chrome.
Hmmm. Never had a problem installing XP (and I've done a lot if installations). Most of them were pretty vanilla, though, so if you have to install things like RAID drivers, SCSI drivers, or other slightly-less-than-mainstream items, I can see where there might be problems.

Until some developer sees an API they like and doesn't run on XP, and breaks the build for the outdated version pretty much.

Depends on the class of key you have, and the release of Office 2000. Some of the editions have activation for some keys.

(Similarly, some editions and some keys of 2003 and 2007 don't require activation. Not sure if that persisted for 2010 or 2013; the MAK and VLK keys I've used with them have all required activation with MS or a KMS server.)

Nah, jury's in. They effed it up. Jury's still out on whether succesors (8.1 being basically a service pack) will recover it.

There's no "likely"; right now IE8 is still reasonably safe with security patches. It will cease to be, rather quickly, next year.

It's not installing XP that's the problem, it's the installation and removal of programs on top of it; it has SOME version of winsxs, which helps avoid DLL hell and programs corrupting the OS for one another, but the file system "virtualization" feature introduced in Vista (plus UAC, plus a version of System Restore that worked significantly more often, etc etc) made a HUGE difference.