Microsoft's new updating "normal" for Windows -- a faster-paced tempo that demands customers apply releases within weeks -- is a first step in moving the OS to a services-style model. But customers may be wary of the change.
But that strategy is going to face resistance from enterprises for years as they struggle to adapt to the new Microsoft and the changes in how it conducts business.
"Microsoft's thinking of Windows as more of a service than using a traditional updating mechanism," said Wes Miller, an analyst with Directions on Microsoft. "That's what they'd like us to get to, thinking of Windows as a service."
With all that implies, added Miller, ranging from frequent updates that include security and non-security fixes, new features and even user interface (UI) changes, to no-questions-asked acceptance of those updates.
"Microsoft would certainly like it to be and it will try to make it so," said Michael Silver, an analyst with Gartner, in an email reply to whether the policies Microsoft rolled out with Windows 8.1 Update and Windows Server 2012 R2 Update were its new normal.
Miller and Silver were referring to the two updates of last week, and Microsoft's initial demand that customers apply them within five weeks or be cut off from all future updates, including monthly security patches. Yesterday, Microsoft extended the deadline for businesses to Aug. 12, but left the May 13 deployment date untouched for consumers.
Even with the extension, Microsoft is forcing commercial customers to deploy those updates in one-sixth of the time it had demanded in the past, when it gave users 24 months -- or slightly longer -- to apply the major updates it had dubbed "service packs."
The problem, as enterprises see it, is that the accelerated pace gives them little time to run the deployment processes they've honed for decades. With those processes, each iteration of an operating system is thoroughly tested to insure it doesn't break existing applications or workflows, then rolled out to a subset of the company's client devices and servers for additional real-world evaluation before finally being re-imaged on all systems to create a homogeneous environment that's easier to support.
"Yes, it does create a problem when business are buying desktops or deploying tablets and trying to have a standard to set to," said Miller. "It's hard to do that when the wheels are constantly in motion and the pieces on the board are always moving."
Microsoft has repeatedly argued that the faster pace -- not just of updates but the limited-time mandates to deploy them -- stemmed from "customer feedback," implying that customers are driving the cadence. "More than ever, these updates are driven by customer feedback and the need to refine and innovate to meet their growing needs," Microsoft spokesman Brandon LeBlanc wrote in a Wednesday blog.
The reality is more complicated. Microsoft might not have had to issue Windows 8.1 Update, or perhaps even Windows 8.1, if it had paid attention to critics' warnings that Windows 8 -- particularly its emphasis on touch and de-emphasis of the traditional desktop -- was too radical a redesign for users to swallow.
And Miller believed there was more at play behind the scenes, especially Microsoft's desire to shift Windows to a software-as-a-service model for updating, if not for revenue.
"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 standardised 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 organisations 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 [email protected].