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."
Sign up for CIO Asia eNewsletters.