The equation corporate IT pros will have to figure out is how long it will take to get all their XP desktops to Windows 7 before XP support runs out, or before application vendors quit producing XP versions of upgrades or new software, which some predict could come as early as 2012.
Windows 7 is the shiny new operating system from Microsoft slated to arrive this year to replace Windows Vista, which after 30 months has failed in the eyes of IT buyers.
Windows 7 offers a host of tantalising corporate features such as AppLocker, DirectAccess, Branch Cache and XP Mode a virtualisation technology that should buy time for users who migrate, but must hold on to key legacy applications.
Gartner predicts that more than half of the corporate Windows user-base is going to skip Vista and aim at Windows 7.
While that means XP users won't have to tangle with Vista in name, it doesn't mean they will avoid the application compatibility issues that gave Vista a black eye right out of the blocks in November 2006. Windows 7 is built on the Vista code base.
"If you are on XP, Windows 7 isn't going to solve a lot of Vista's migration problems," says Brett Waldman, a research analyst for IDC. "Going from Vista to Windows 7 should be a much easier transition than XP to 7."
Users who have deployed Vista have an easier path because Microsoft provides an upgrade option not available to XP users, and because they have already solved their application compatibility issues.
Microsoft says nearly all applications that run on Vista will run on Windows 7 and early testing by users is beginning to validate that claim.
In addition, hardware upgrades made for Vista are relevant for Windows 7 rollouts.
While those rollouts won't be painless for Vista converts, it is those on the XP side who will have to tap into their planning and organisational skills.
The XP equation
The predominant migration questions among those coming off XP are "when" and "how".
"What we are saying is that by the end of 2012 you should be off XP," says Michael Silver, vice president and research director at Gartner. With most large corporations taking 12 to 18 months to test and pilot a new operating system, the migration clock is ticking.
"If I target the end of 2012 to get XP out then you have your migration window," he says. "Organisations really need to be poised to do a lot of migrations on new machines and some existing ones in 2011 and 2012. That will be the mainstream of the migrations."
Silver says Gartner's recommendation is a conservative one that provides a 15-month buffer before XP support ends on April 8, 2014. Mainstream support for XP ended in April 2009, just a year after XP SP3 shipped.
Microsoft for its part told XP users last month that if they are just starting to test Vista they should switch to Windows 7.
Silver recommends users in that boat switch only if it means less than a six-month delay in their current planning. "You don't want to lose momentum. If you have already done lots of testing or might be set to deploy you should continue with Vista," he says. "One of the big issues here is that Vista is a difficult decision politically at this point, but those that have migrated to Vista are generally happy."
Hitching the migration horse to the Windows 7 wagon, however, doesn't mean users won't have to take along issues that polluted Vista acceptance.
Applications that were not compatible with Vista won't work on Windows 7. The new XP Mode, available with professional, ultimate and enterprise editions, will give users a bit of a respite, but not a panacea.
With both Windows 7 (the host operating system) and XP (guest) running on a single machine, users will be forced to maintain and patch two operating systems per desktop.
Analysts such as IDC's Waldman and Gartner's Silver say it's a short-term solution.
"To take full advantage of new enhancements in Windows 7, which is what users are paying for, the app needs to be built for Windows 7," Waldman says. He says XP Mode is likely a one to two-year Band-Aid.
Users are gearing up
"XP Mode might be the way we get around the fact that some of our institutional apps are behind the technology curve. It could be the answer," says Jeff Allred, manager of network services at the Duke University Cancer Centre. He says patch management tools will make it easier to manage two operating systems on a desktop and that XP Mode's administrative considerations are not a showstopper
Allred is in the process of testing Windows 7, which he says is faster, more stable and seems leaner than Vista. "We are much happier with Windows 7 RC than Vista in its full shrink-wrap version," he says.
He says a Vista migration would have meant upgrading 60% of his hardware, something he was not prepared to do. With Windows 7 and its smaller footprint, the majority of his hardware is already compatible.
The same is true for Wesley Stahler, senior system consultant at Ohio State University Medical Centre, who is testing Windows 7 from an Asus Eee netbook.
He says the medical centre is just now beginning migration discussions to move off XP.
"We have some clinical-based apps that work great on [Internet Explorer] 6, but on IE 8 [with Windows 7] not so much. Those are the things we will have to look into," he says.
He says XP Mode might help, but "as someone who has to maintain the environment I would prefer not to support two operating systems."
Stahler says there are other features that are enticing or will help save money.
"Right now we are using two different products to do what BitLocker can do, so we could save money and administrative headache," he says. BitLocker is a full-disk encryption feature introduced with Windows Vista and available in Windows 7.
For its part, Microsoft is offering a range of migration tools to help with a move to Windows 7.
Microsoft also has added tools to its Windows Automated Installation Kit (WAIK), specifically to ease the management and deployment of Windows images.
The Windows System Image Manager lets users do low-level customisation of an operating system image. The tool works with System Centre Configuration Manager, which adds an administrative UI that lets users replicate information across their network. Integration with System Centre management tools supports rollouts that scale to enterprise deployments.
Windows 7 also features updates to Microsoft's ImageX command-line tool, which lets users capture, modify and deploy Windows images. The tool is rolled into Configuration Manager and given a GUI interface.
Deployment Image Servicing and Management also is part of WAIK and is used to apply updates and drivers to Windows' images.
Microsoft is also updating its User State Migration Toolkit with a new feature for hard-link migration, which keeps desktop data on the machine during the operating system upgrade, cutting deployment time from hours to minutes.
And the forthcoming Microsoft Deployment Toolkit (MDT) 2010 is an updated version of the Business Desktop Deployment Kit that shipped with Vista. It is now integrated with System Centre Configuration Manager and builds off WAIK tools. Microsoft will release version 6.0 of its Application Compatibility Toolkit once Windows 7 ships.
"The capability to centralise and bring into one admin console the ability to customise and deploy an [operating system] with applications and updates is where the Windows division with System Centre is a great story," says Jeff Wettlaufer, senior technical product manger for System Centre.
Now the only other story left to tell is if Windows 7 will deliver on its promises.