"This is a once-in-a-decade movement," IDC analyst Al Gillen says. "People that move to Windows 7 can expect to be on Windows 7 for a pretty long life cycle, much like we have with XP today. So whatever you do, and whatever decisions you make are decisions you're going to have to live with for a long time."
But many organizations face problems because of insufficient planning. According to a Gartner report, most organizations undergoing Windows migrations "underestimate how long it will take them to [test applications and fix problems]; don't build a business case or properly track the benefits of their projects; [and] allocate insufficient time for their pilot."
There are probably too many Windows 7 migration issues to list in a single article. But here are five tips to help you on the path to Microsoft's latest operating system.
1. Virtualize applications and user settings
Desktop virtualization commands much of the attention in the IT market today, with some vendors saying the technology will ease migration to Windows 7. But this isn't the only type of virtualization that can make Windows 7 upgrades and future OS migrations easier than they might otherwise be.
Two technologies to consider are application virtualization and user virtualization. Nik Gibson, the enterprise desktop practice leader at Forsythe, a technology consulting firm, has worked with many large enterprises on virtualization projects, and says it's often easier to virtualize applications than desktops. "We see that a lot. It takes longer to virtualize the desktops than the applications," he says. "The desktops are more unique," with various use cases depending on the employee.
Gibson says "virtualize your applications" is the first tip he would give to customers planning a large Windows 7 migration. "And that just makes sense," he says. "If you can decouple your applications from the base operating system, it's going to be easier to migrate that operating system."
Application virtualization will not only aid the current move to Windows 7, it will also make future upgrades to Windows 8 easier too, IDC's Gillen says.
Application virtualization isn't exactly new, but has undergone a bit of a marketing makeover in the past few years. What Citrix used to call its Presentation Server product for application streaming is now referred to as XenApp and labeled a "virtualization" technology. VMware's ThinApp, based on technology acquired in 2008, is another option in this market.
But application virtualization won't help move each user's personal data and settings from one OS to another to another. That's where user virtualization comes in. Software such as VMware's RTO and AppSense's user virtualization product will take a user's profile, data files and settings, and move them easily from one machine to another, for example from a Windows XP computer to one with Windows 7, Gibson says.
User virtualization is still maturing, though. Although VMware acquired RTO technology in February, it has not yet integrated the software into its desktop virtualization product.
Microsoft itself offers a User State Migration Tool to ensure that user settings and files survive OS upgrades. AppSense technology is on the market, and can be used for Windows 7 migrations both on physical PCs and in conjunction with virtual deployments. Another user migration toolkit is available from Tranxition, which can also be used for migrations involving either physical or virtual desktops.
2. Test applications to prepare for potential incompatibility
In a Gartner report titled "Pitfalls to Avoid on the Road to Windows 7 and Office 2010 Migration," analyst Michael Silver says organizations need to test applications on Windows 7 to make sure they will run and also determine whether the makers of the applications will support them on Windows 7.
"Most organizations have more applications than they know about that users consider to be important or critical," Silver writes. "Many organizations that have tested applications for Vista believe that these programs will run with Windows 7, but ISVs often limit support to specific versions."
For critical applications, which may carry financial and legal risks if they fail, "lack of ISV support may represent too much risk to move to Windows 7," he writes. A decade ago, "Windows 2000 Professional broke a lot of applications," Gillen says.
With Windows XP, Microsoft created some compatibility tools to run earlier applications. But if an application made it onto XP only because of the compatibility tools, there's no guarantee it will run on Windows 7, Gillen says.
Complicating matters even further is that some customers use Web-based applications that work only on Internet Explorer 6, an out-of-date Web browser that is two releases behind the IE8 that comes pre-installed on Windows 7.
Some companies are spending money to buy new applications or upgrade existing ones so they will work with Windows 7 or new versions of Internet Explorer. Although expensive, this is often the best long-term approach.
"Our research tells us customers are very much looking forward to Windows 7," Gillen says. "They realize it's not going to be a completely smooth transition. The life cycle is over on XP and customers get that."
3. Use Windows XP Mode -- but not for long
Not every application has to make the move to Windows 7 immediately. That's because virtualization technologies let older applications run on guest operating systems. Microsoft's virtualization technologies include Windows Virtual PC, MED-V (Microsoft Enterprise Desktop Virtualization) and the related Windows XP mode, which lets you run a virtual instance of XP on a Windows 7 desktop.
"It's a definite option for people," but is usually not the first choice for a widely used application, says Nortec consultant Tim McGilvery. "It usually is one or two users."
XP Mode is a surefire way of supporting XP-based applications on Windows 7, but Gillen says it shouldn't be used as a long-term solution. Rather, it should simply be used to ease the transition between XP and Windows 7.
Challenges include the fact that "you have two operating systems to manage and be responsible for," Gillen says. "If you're running XP Mode, it doesn't take away the fact that the base operating system is out of Mainstream Support. It solves the short-term compatibility problem, but it doesn't solve the long-term migration problem."
Microsoft recently ended support for Windows XP Service Pack 2. Service Pack 3 is eligible for support until April 2014, but only for "Extended Support," rather than the more comprehensive Mainstream Support.
4. Get your licensing straight
OS migrations can be costly. Gartner estimates that moving from Windows 2000 or XP to Windows 7 costs between $1,035 and $1,930 per user, while an upgrade from Vista to Windows 7 costs $339 to $510 per user.
The Gartner cost model is based on 2,500 users and involves many factors including labor, training, systems integration, application development and hardware acquisitions. The difference between migrations from XP and from Vista is explained by extra costs related to testing and fixing applications and replacing hardware. (A machine that runs Windows Vista could be upgraded to Windows 7, and applications that run on Vista can likely operate on Windows 7).
The cost of Windows licenses is part of the Gartner equation, and has also been examined in detail by Directions on Microsoft analyst Paul DeGroot.
DeGroot says in a worst-case scenario, customers can pay three times for the same Windows license -- once for the OEM license that comes with a physical desktop pre-installed with Windows; once for an "upgrade license" as part of a volume licensing plan, and once again for Software Assurance, which guarantees access to new software versions.
Windows 7 Enterprise is available only to Software Assurance (SA) customers, so avoiding that payment is difficult. But there are a few strategies to consider, DeGroot said in a recent Network World article titled "5 tips for managing Microsoft licensing costs."
Customers can purchase the "Open License," which lets them buy Software Assurance for two years rather than three. Although SA rights will expire after two years, the customer has the right to use Windows 7 Enterprise indefinitely. Microsoft's "Select" agreements also offer discounts by letting customers purchase Software Assurance for terms shorter than three years.
Customers should remember it's always smart to negotiate, particularly when certain portions of Microsoft licensing agreements seem inflexible. Analysts say Microsoft is often willing to give discounts, particularly to large customers with thousands of desktops.
5. Plan ahead -- and then plan some more
This may seem too obvious for words, but Windows 7 migrations require a significant amount of planning. Unfortunately, IT organizations all too often fall short in this area, according to Gartner. Windows 7 pilots should last at least three months and include a first phase for pushing Windows 7 out to a group of users to ensure that all applications work; a second phase to improve the deployment process; and a third phase focusing on education and support.
"Many enterprises plan pilots as short as a few weeks," Gartner's Michael Silver writes. "Shortening the pilot increases risk significantly and often results in logistical and compatibility problems during deployment, which makes the project look less successful to the users. A project the user community deems unsuccessful cannot be considered a success by the IT department."
One organization that takes this advice to heart is Del Monte Foods, a San Francisco-based food production and distribution company, which plans to upgrade 3,000 business users to Windows 7 over three years.
David Glenn, director of enterprise operations for Del Monte, says his company is piloting Windows 7 within its IT organization, representing 140 users across the country. Network testing is one of the key factors. Del Monte is examining how various applications perform over different network connections, and is in general finding good results.
"Windows 7 does offer a lot more stability and performance capabilities than XP did," he says.
If your company is still primarily a Windows XP shop, it's time to start planning for Windows 7 now even if you don't plan to upgrade all desktops immediately. XP support ends in 2014 but software vendors are "unlikely to support new versions of applications on Windows XP starting in 2011 [and] by 2012 it will be common," Gartner says. By 2013, few new PCs will include Windows XP drivers.
Microsoft is technically offering Windows XP "downgrade rights" until 2020, but for the reasons stated above few businesses are likely to take that option.
The speed of a company's Windows 7 migration will vary based on the age of its hardware, whether it is running on XP or Vista, the types of users it has and other factors including the length of its typical PC refresh cycle.
Moving from Vista to Windows 7 should be a lot easier than moving from XP because of application compatibility, Gillen says. "If you've already deployed Vista, you've done 95% of the work," he says. Although most OS refreshes occur when companies roll out new PCs, it's only practical for a company with Vista PCs to upgrade those same PCs to Windows 7.
Regardless of whether the upgrade happens over the course of a few months or is phased in over a couple of years, planning should happen far in advance and IT departments should consider all the new technologies that make desktop management more efficient, including desktop virtualization.
Instead of simply porting existing applications to Windows 7 and "recreating the architecture you've lived with for the last decade," Gillen says "my advice to customers is to seriously consider all the options they have."
The goal is to make the end user migration quick and easy, but "it's not a quick process for the IT department," Gillen says.