It's less than a year until Windows XP support runs out. This is hardly a small, isolated issue — studies suggest that XP accounts for more than 40 per cent enterprise desktops in the UK, for example.
Microsoft is trying to woo customers into upgrading with special offers, but businesses may have a harder decision than ever before when it comes to making up their mind about updating their desktop infrastructure.
That's because the organisations which have been slumbering under their cosy XP duvet for so long will wake up in a very different technology environment to that of 2001, when the now venerable operating system was released.
They'll have to get to grips with a far wider choice of operating systems and hardware, plus a very different Microsoft, and that means for some organisations the decision to swap Windows XP for a later iteration of Windows might not be the automatic move that it would have been even two or three years ago.
And, for Microsoft, the timing on this is all a bit tricky. It's still early days for Windows 8, and its new user interface in particular has unsettled many. So for some companies looking to ditch XP, the need to train end users to use the new UI in Windows 8 may be a concern for them.
Windows 8 has been seen as a transitional operating system, bridging the old and the new (signalling the dawn of Microsoft as a services company). For companies contemplating the leap, even if they jump to Windows 7 (a more likely option for many) they'll know that that big change is coming to Windows.
At the same time, there is a new crop of rival operating systems that are enterprise-credible ready to tempt businesses, including Linux variants and the likes of Android and iOS for those braver souls contemplating embracing a mobile or tablet-only environment.
On the hardware side, many organisations using XP will want to junk their antique kit at the same time as adopting a new OS.
That means that they ought to be open to new form factors as well new operating systems: or even new operating system and new form factors. That could open the door to tablets like Apple's iPad or even Google's Chromebook, even if it is only small trials.
As Ovum principal analyst Roy Illsley puts it, companies have to decide what the desktop should look like. "That might help them because they might decide, 'Only 25 percent of our estate really needs to be desktop PCs, and that 25 percent of desktop PCs we can do the upgrade from XP to Windows 7 within 12 months. The other 75 percent could go mobile or to tablets or straight onto a new platform," he said.
Now, you could argue that many of the organisations still hanging onto XP are by definition late adopters and are thus unlikely to want to risk leading-edge, let alone bleeding-edge, technology. But these organisations are also likely to be holding onto XP in a death grip because they're short of cash.
That means they might be more open to new ways of thinking, and cutting their IT costs, than they otherwise might - that might lead to more hybrid deployments and experimentation.
Most organisations will of course eventually make the upgrade to a newer version of Windows – but the days of the unquestioned monolithic upgrade are long past.
Take the TechRepublic poll: what percentage of your enterprise is running Windows XP?