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For organizations waffling about migrating to Windows 7, especially those still running Windows XP, the clock is ticking.

According to analysts at Gartner, it takes 12–18 months to prep for a client operating system change. That’s a year to a year and a half of application testing, dealing with issues the tests reveal, and overall planning. Then there’s the actual migration which, as administrators know only too well, can take a significant chunk of time in itself.

Plus, since support for Windows Vista RTM (the original release with no service packs applied) has ceased, Windows XP SP2 support will stop in July 2010, and even extended support for Windows XP SP3 will end in April of 2014, the experts agree that the time to move is sooner rather than later.

Mark Tauschek, research director at Info-Tech Research, thinks that Windows XP shops are most at risk. For organizations running Windows Vista (admittedly, he says, a very small percentage) with Service Pack 2, there’s no pressing need to move, and a Windows 7 upgrade could get expensive for them unless they have Enterprise Agreements or Software Assurance that allow them to upgrade for free. However, he says, for Windows XP shops, “While formal end of life (for XP) is April 2014, by 2012 they will run into situations where they can’t find drivers or application updates. They have to think about migrating to Windows 7.”

Independent analyst Carmi Levy agrees. “Latecomers could begin to experience driver incompatibility issues and security lapses, as Microsoft and third-party vendors gradually shift their attention away from Windows XP,” he says. “There’s a cost associated with holding on to any technology for too long, and we now have a bubble of enterprises at risk of sticking with the XP horse well past its due date. This makes Windows 7 an even more critical migration target than would otherwise be the case.”

Expeditious migration planning becomes even more critical if you look at Microsoft’s support lifecycle matrix. Once a product is out of mainstream support, only security-related patches are produced for it, and even those are only for supported service pack levels (which means, for Windows XP, SP3). If a non-security issue that needs patching arises, you’re on your own; and if you’re looking for answers to questions, break out a credit card because those answers now come at a price.

Another price of clinging to Windows XP is beginning to reveal itself as well; new versions of software (both applications and device drivers) may not run on it. For example, Microsoft has already announced that its upcoming Internet Explorer 9 will only work on Windows Vista or higher. This is not an arbitrary decision; architectural components for graphics and security required by IE9 didn’t even exist in Windows XP’s heyday.

On the other hand, some organizations find themselves trapped by older mission-critical applications that don’t run on newer OSes. “This happens a lot with ERP installations where there was a fair bit of customization,” says Tauschek. “Customers can’t upgrade [the ERP software] because it would break their customizations.”

This points to the need to look at applications now. Tauschek adds, “Regression testing of applications working together under Windows 7 is the biggest planning point, especially with home grown applications.” He recommends that companies both use Microsoft’s compatibility testing guidance and devise their own tests.

Microsoft is, of course, anxious to help customers move to Windows 7, for many of the same reasons cited by the analysts. Says Elliot Katz, senior product manager for Windows Client at Microsoft Canada, “It is important for companies to have begun their migration process so they can gain the benefits of all the advances in Window 7 sooner rather than later. For companies migrating from Windows XP, it’s also important to be fully deployed before application vendors stop supporting their Windows XP applications.”

The other half of the equation is hardware. Microsoft offers assistance in assessing hardware compatibility as well. And, Tauschek points out, Vista-compatible hardware will likely run Windows 7, so newer computers should be fine, even if they were downgraded to XP. “The bigger issue is with drivers for older printers, plotters, scanners, and so forth,” he explains. “You might find that some devices don’t have Windows 7 drivers.” Though, he adds, it may be possible to use those devices in Windows 7’s virtualized XP Mode, which is also a potential solution for issues around incompatible application software.

“Ideally, OS migration should be tied to hardware migration,” Levy notes. “This strategy minimizes the disruption to end-user productivity because it combines both upgrades – OS and PC – into one event. Upgrading the OS on existing PCs leaves open the potential for two disruptive events. Worse, it opens up the potential for incompatibilities between the new OS and hardware that was never designed with it in mind.” A lot of companies have adopted this strategy, deploying Windows 7 over a couple of years in conjunction with a hardware refresh, according to Tauschek.

However an organization does it, the analysts agree that the migration to Windows 7 should be completed in 2012, and planning should be underway now. “Some companies say that they won’t move until something compels them to,” Tauschek says, “but when something compels them, it’ll likely be too late and they won’t have time to prepare.”

“It’s kind of a world of hurt,” he adds.

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