Windows Blue and Microsoft's continuous upgrade strategy

Analysts uneasy about how enterprises can keep up with a faster clip

Microsoft yesterday confirmed Windows "Blue," an upgrade to Windows 8, but analysts remained uneasy about how the faster release cadence that Blue represents will be digested by businesses.

"Microsoft is going to be on an annual release cycle, and enterprises will have to figure out how to get used to it," said Frank Gillett of Forrester Research.

Blue, the code name bandied about for months by Microsoft-centric bloggers like Mary Jo Foley of ZDNet and Paul Thurrott of Super Site for Windows, exists, said Frank Shaw, the head of Microsoft's communications group, on a company blog Tuesday. He did not say, however, when the upgrade will debut, whether Microsoft will follow its traditional path of offering public previews to customers prior to its launch, or even whether it come with a price tag.

Most, however, believe that Blue will land this summer, likely after the BUILD 2013 developers conference gives Microsoft a chance to show it off. BUILD 2013 will take place June 26-28 in San Francisco.

And it's probable that Blue will inaugurate an annual upgrade schedule, where Microsoft issues smaller-scale updates to its newest OS at a faster pace than the historical average of around three years between Windows editions.

Shaw was clear about Blue's purpose and how it fit into Microsoft's self-professed transition from a software developer to what CEO Steve Ballmer last year dubbed a "devices and services company."

"This continuous development cycle is the new normal across Microsoft," Shaw said. Microsoft, he added, has "a clear view of how we will evolve the company" with "plans to advance our devices and services, a set of plans referred to internally as 'Blue.'"

How that kind of schedule -- annual, or as Shaw put it, "continuous" -- plays to Microsoft's core customers, including enterprises and government agencies, is a big question.

Large organizations are notoriously conservative in their adoption of upgrades, and for good reason: They worry that without comprehensive testing an update could break a critical workflow.

This week's updates to three core Windows 8 apps provided a perfect example. Microsoft's refresh of the Calendar app disabled synchronization with the cloud-based Google Apps for Business suite. Any firm running Google Apps that told workers to apply the Calendar update would have found the latter useless.

Nonetheless, Patrick Moorhead, principal analyst at Moor Insights & Strategy, said this year is too early to find out whether enterprises could adopt to the faster release tempo.

"Commercial hasn't started deploying Windows 8 yet," Moorhead said. "Maybe in a couple of years, when Windows 9 is out and both enterprise and consumers are deploying the operating system, an update like Blue -- that adds features to the UI -- could change, for example, training [in businesses]. But it's way too early to know if [the faster pace] is a positive."

Michael Cherry of Directions on Microsoft, a Kirkland, Wash. research firm that specializes in tracking Microsoft's moves, agreed that there were too many unknowns -- and too few knowns -- to predict how, or even if, businesses will climb on the faster release train.

"What are the mechanics of doing the roll-outs?" Cherry asked. "Is it a clean process? Microsoft has improved their imaging tools a lot, but there has to be a compelling reason to upgrade [for enterprises]. Even if these updates are free, I still have to incur the expense of rolling them out."

Few companies can afford a permanent deployment staff to push frequent OS upgrades to employees, Cherry noted. But to keep up with Microsoft's clip, enterprises without such a staff will be forced to pull IT personnel from other projects to handle the annual upgrades.

That won't go down easy at enterprises.

Corporations often take years to roll out a new operating system, and often skip editions as a result: That's what happened when businesses migrated from Windows XP to Windows 7, sidestepping Vista. And the same process will probably repeat, as companies that only recently wrapped up their Windows 7 deployments take a breather and avoid Windows 8.

But whether that approach can work with an accelerated release cycle remains a mystery.

"Service packs perform a different role," Cherry acknowledged, referring to the irregular bug fix and security patch roll-ups that Microsoft has issued in the past for Windows. Even so, he turned to the service pack (SP) example in the absence of anything better.

"There's a window of time to do a service pack," Cherry said, talking about the past policy of a 24-month stretch after the release of an SP to migrate from the prior version. "But if the cadence is annual, you might be behind several 'Blues' two years after [the release of the initial version]. Can you [upgrade to] Blue 2 directly, or do you have to do Blue 1 first, then Blue 2? There's so much we don't know yet."

Even Microsoft's licensing practices could play a part if Redmond doesn't modify the terms of its "client access licenses," or CALs, that let client systems -- desktops and notebooks now, tablets, too, in the future -- connect to servers.

According to Cherry, as soon as a company puts its first upgraded server into production, the firm must update all its CALs. And with Windows Server 2012 also apparently slated for a "Blue" update -- hinting that the server software will also be upgraded annually -- that would mean a yearly CAL refresh, too.

Moorhead countered, speculating that the annual updates may be easier for enterprises to assimilate than everyone anticipates. "I see these as not much of a major launch at all," Moorhead said of Blue. "The features could be those that didn't make the cut for Windows 8. It's doesn't sound [as aggressive as] Apple's annual cycle."

Or corporations could, as they often do now with service packs, simply ignore the annual updates and in several years, migrate to, say, Windows 9 but turn their backs on refreshes.

Unless Microsoft offers more than what Blue portends, Cherry believed enterprises simply won't bother. That would make Microsoft's strategy moot for all but consumers and the very small businesses which behave like consumers.

"The problem here has to do with what functionality is actually there," said Cherry. "The functionality of Windows 8 is so poor that I don't care if they do release Blue. For the OS itself, the bigger problem Microsoft has with Windows 8 is that most of us are using it in Windows 7 mode."

According to Cherry, enterprises are still searching for the value in the Windows 8 model, which combines a classic Windows 7-style desktop with the radical "Modern" UI, the touch-first, tile-style, app-based user interface many IT professionals believe is better suited to tablets and unwelcome on traditional PCs.

If businesses reject Microsoft's revamped Windows strategy -- which shows signs of deprecating the desktop, even eliminating it -- and thus the concept of faster releases, Microsoft could be in trouble: The bulk of its revenue is ultimately dependent on Windows being the choice of corporations.

But faster updates are here, and they're not going away, said Moorhead, echoing the comment of Forrester's Gillett, who said enterprises simply must figure out a way to deal with annual Windows upgrades.

"It's not just a feeling that the rate of change has increased, it really has," said Moorhead. "Microsoft has to be quicker."

He admitted that meant Microsoft has a difficult selling job ahead of it. "They're going to [be] under pressure to keep corporate customers happy, and still have a viable consumer OS that keeps up with the fad of the year," said Moorhead. "It's going to be really tough. IT was given years and years and years on XP, and wasn't forced to go to Vista. Microsoft let them slide. I don't see how that's feasible now."

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 © 2013 IDG Communications, Inc.

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