A few times over the last year, I’ve had conversations with people about Windows XP holdouts. That is, that as Windows XP’s impending doom rapidly approaches next April, businesses and consumers holding out on Windows XP will readily flock to something new, such as – ideally for Microsoft, Windows 8.1 – or Windows 7.

I’m not so sure.

To start, let’s consider why a business or consumer would still be running Windows XP today. Most likely, it’s a combination of all of the following:

1. It’s paid for (the OS and hardware)
2. It runs on the hardware they have
3. Applications they have won’t run, or aren’t supported, on anything newer
4. It requires no user retraining
5. They don’t see  a compelling reason to move beyond XP
6. They don’t realize the risks of sticking with XP after next April.

You can split those reasons into two categories. Items 1-3 are largely due to financial impediment, while 4-6 are generally due to “static quo” – XP meets their business needs and 8.1 or 7 doesn’t provide the necessary pull to motivate them to move off of XP.

It’s not that 7, 8, or 8.1 did anything wrong, necessarily. I was there when XP shipped, and I’ll tell you I heard many business customers complain about numerous things. They hated the theme and felt it was toy-like. They wanted to be able to take off Movie Maker, Internet Mail & News, or other consumer niblets of the OS, but couldn’t. Frankly, some of them just felt it was a warmed over Windows 2000 (obviously none of those customers had ever tried to undock a hibernated Windows 2000 laptop). For many customers, it took until XP had been effectively re-released as XPSP2 for them to really fall for it. When Vista shipped, reasons 4 & 5 above largely doomed it. Vista had a completely nebulous value proposition for most consumers and almost every business, leading to Windows XP becoming even more deeply engrained into many businesses.

Many people describe Windows 7 as “a better Windows XP”, which I think is actually an insult to both operating systems. But frankly, unless a business understands item number 6 (which Microsoft just grabbed a drum and started beating really hard – albeit very, very late), the rest don’t matter.

I’ve talked to several businesses about Windows XP over the past several years. For better or worse, most of them are happy with the hardware and software investments they made over the last 12 years, and many don’t feel like spending money for new hardware (especially new touch-centric form factors with value that they don’t see clearly yet).

Even more important though, is the number of times we have run into businesses – especially small businesses like dental, medical, or other independent practices – which during the past decade either bought commercial software packages or hired consultants to build them custom software. As a result, many of them hit item number 3 – “Applications they have won’t run, or aren’t supported, on anything newer”. I kid you not, there are a lot of small businesses with a lot of applications that honestly have no path forward. They cannot stay on XP – they cannot be secure. They cannot move off, as they either cannot find a replacement of one or more of their key applications, cannot move that key existing application, or in some cases, simply cannot afford to move to a replacement (in case you haven’t noticed, we’re still not in a great economic climate). They are stuck between a rock and a hard place. Move off of XP and throw away working systems your employees already know for new systems with unknown features or functionality. To boot, any of these new solutions are primarily still targeting Windows 7 (the desktop), not the Windows 8+ “modern UI” – diminishing some of the key value in acquiring tablet or touch-centric devices running 8, if the system is, for the time being (and likely for the foreseeable future) stuck on the desktop. Since Windows 8+ doesn’t include Windows XP Mode, unless a customer has appropriate enterprise licensing with Microsoft, they can’t even run Windows XP in a VM on Windows 8+ (and I have a hard time believing that customers who spend that kind of money are the kind of customers who are holding out).

There are still many organizations that are using XP (and likely Office 2003) and appear to have no exit strategy or plan to leave XP behind. It appears a lot of organizations don’t realize (or don’t care) now porous Windows XP will become after it ceases being patched in April. It isn’t a war-hardened OS, as some customers believe. It’s a U.S.S. Constitution in an era of metal battleships. I hate to sound like a shill, but XP systems will be ripe for an ass-kicking beginning next spring, and they can, and will, be taken advantage of. I also don’t believe Microsoft will do any favors for businesses that stay on XP (and don’t pay the hefty costs for custom support agreements with a locked and loaded exit plan in place).

XP is dying. But I believe lots of organizations are simply unclear about what kind of threat it poses to them. As a result, they’re sitting on the investment they’ve already made.

I also think that a lot of organizations that are still sitting on XP today may even be aware of (some of the) potential risks that XP poses to their organization after April, but simply don’t have the budget to escape in time, even if they had the motivation (which lots of them don’t appear to have). Even if a company pulls the trigger today, if they have any significant number of XP systems and XP dependent applications, they’ll be lucky to be off of XP by April.

There’s a belief that a lot of these customers had budget sitting there, had no app blockers, and might have even wanted to go to 7, 8 or just “something new”, but were just lackadaisical and for some reason will now get a fire lit under them, generating a windfall of sorts for Microsoft, PC OEMs, and partners over the next 5 months. Instead of that easy opportunity, I believe where you run across XP in the majority of organizations at this point, a better analogy is a set of four fully impacted wisdom teeth in a patient with no dental coverage.