Windows' new normal shows software-as-a-service ambitions

But the more Microsoft pushes change, the more enterprises will resist

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"It's a weird Catch-22," Miller said. On one hand, Microsoft is advocating rapid acceptance of operating system updates to bring Windows into the 21st century, where mobile OS updates are not only frequent for competitive-advantage reasons, but where the majority of users readily accept them. On the other, enterprises dislike change and can point to flaws in Microsoft's current updating processes, like the one last week that suspended delivery of Windows 8.1 Update and Windows Server 2012 R2 Update for seven days, as reasons not to trust Microsoft.

The result, said both Miller and Silver, will be retrenchment by enterprises, which have standardized on Windows 7. In the face of Microsoft's attempt to deliver Windows in a more service-style model, they expect companies to hold onto Windows 7 longer and more passionately than they might have sans the successor's accelerated pace.

"It's really unclear how organizations that have compliance and validation requirements like healthcare and pharma will be able to keep up," said Silver. "They will likely have to sit on Windows 7 until they can figure it out."

"Microsoft wants people to be deploying Windows 8.x in the future," said Miller. "But what I fear is that a lot of businesses will hold back and wait with Windows 7."

Neither analyst believed Microsoft would monkey with Windows 7 in the same way it's updating Windows 8.x. "Windows 7 is much more likely to be left alone by Microsoft," said Silver.

"I don't expect another service pack for Windows 7," echoed Miller. Microsoft last shipped a Windows 7 service pack in February 2011, and has given no hint that it will follow with an SP2.

The uproar if Microsoft did change Windows 7's updating practice would be enormous. And therein lies Microsoft's between-a-rock-and-a-hard-place situation: It wants to change how it does business, but the more it does the harder enterprises' heels dig in.

As an illustration, Miller contended that many of Microsoft's moves to quell the unrest generated by Windows 8 and even those to support legacy scenarios -- such as IE11's Enterprise Mode that improves rendering of websites designed for IE8 -- are threats to the company's efforts to drag customers into the future.

"Things like bringing back the start menu are in fact a bad story for Microsoft," said Miller, who argued that the more Microsoft makes Windows 8.x like Windows 7, the more the latter seems "good enough" to stick with. Why change if the change doesn't have benefit?

"Some people will decide to get on the [fast-update] train and live more dangerously. But there are a lot of business stalling out [on updates, whether upgrades from XP or potentially from Windows 8.1 to Windows 8.1 Update] and sitting on known issues," Miller said.

The faster cadence also threatens Microsoft's push to get customers into cloud-based services, Miller asserted. "If people are uncomfortable with software-as-a-service [through rapid updates], they're going to be even more uncomfortable with the cloud."

Gregg Keizer covers Microsoft, security issues, Apple, Web browsers and general technology breaking news for Computerworld. Follow Gregg on Twitter at  @gkeizer, on Google+ or subscribe to Gregg's RSS feed . His email address is

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Copyright © 2014 IDG Communications, Inc.

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