Companies that are still running Windows 7 should start planning now to upgrade their systems if they want to avoid problems transitioning to the successor to Windows 8, currently known only as “Threshold," according to analysts from research firm Gartner Inc. Microsoft is planning to offer support for the popular OS until 2020.

“The end of support for Windows 7 will be January, 2020, assuming there are no changes to its current support life cycle,” Stephen Kleynhans, research vice president at Gartner said in a blog post on Tuesday. “While this feels like it's a long way off, organizations must start planning now, so they can prevent a recurrence of what happened with Windows XP.”

Memories of a Debacle

According to Gartner, many IT departments found themselves scrambling when Microsoft pulled support for the XP operating system. Almost 25 percent of all PCs were still running XP when support ended, forcing a rushed and chaotic transition to Windows 7. Enterprises and organizations now find themselves in a very similar situation: four-and-a-half years remain until Windows 7 is put out to pasture, roughly the same amount of time Windows XP had left when Windows 7 was first introduced.

But just because organizations should start planning their migrations now does not mean they should rush to implement Windows 8, the latest version of Microsoft's OS, immediately. In fact, Gartner argues against removing Windows 7 from existing machines in favor of Windows 8. “We see little value in doing this, and do not recommend it without a solid business case,” Kleynhans said in the blog post.

Instead, Gartner recommends one of two strategies for enterprises to migrate away from Windows 7. The first option is to install Windows 8 on new machines as they are acquired. This strategy gradually shifts an organization's implementation away from Windows 7 over time.

The second option would be to skip Windows 8 altogether, and wait until Microsoft releases its Threshold version, or perhaps even the version after that, depending on how much of a upgrade over Windows 8 Threshold represents. “We believe most organizations will do this,” Kleynhans said.

Although likely to be a popular strategy, the second strategy comes with a risk: many companies adopting this method will likely still be using Windows 7 when implementation ends.

Smoother, But Still Bumpy

The good news is that Microsoft has made some changes to the way it rolls out its upgrades that should make things easier for IT managers. “Microsoft has moved to a more fluid approach to releasing and updating Windows,” according to Kleynhans. “In the 18 months since its release, Windows 8 has had two significant updates, and we expect more during the next year.”

Companies that are already running Windows 8 on some of their devices, should not avoid deploying new devices on the OS. However, Windows 8.1 Update 2 is likely to enter the market soon, so it may make sense for IT managers to hold off on a broad roll out until then.

Although Microsoft has made the upgrade process smoother, companies are still likely to encounter some speed bumps along the way. Organizations requiring compliance and application validation will likely find that deploying Windows 8 and keeping current may be impossible. Consulting with software providers will be necessary to ensure their applications are fully supported and validated.