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."