Moorhead, Gillett and Milanesi all cited the disappointing debut of Windows 8 and Windows RT on tablets, and Microsoft's inability, even after several years, to make solid gains in smartphones with its Windows Phone operating system, for their pessimism. And Milanesi's forecasts -- which assume that five years from now, about four-fifths of Windows devices sold will still be PCs, not tablets and phones -- weren't much help.
But they also all said Microsoft was showing some encouraging signs, notably "Blue," the code name for both a refresh of Windows this year and for an multi-year initiative designed to dramatically increase the development and release tempo of the platform to put it on a more equal footing with the pace of mobile operating systems.
Microsoft has time to correct its course, although that window is closing.
"2013 is still a transitional year, I think, even from a consumer perspective," said Milanesi. "But 2014, starting with this year's holidays, is where we need to see some momentum from Microsoft. Blue getting to market and different form factors may be the start."
Last month, Microsoft relaxed a Windows 8 and Windows RT certification rule to allow lower-resolution devices, which analysts said signaled that smaller, less expensive Windows tablets are in the offing.
Gillett, of Forrester, echoed Milanesi's timeline. "Things will be sideways until next year," he said. "It's still so early in Windows 8 and Windows Phone 8."
But any way they looked at it, the analysts saw Microsoft at a point that will make or break its influence. If it can regain its mojo by grabbing consumers' attention, it will continue being a critical part of the technology landscape. If it can't, well....
"They need to get this," said Milanesi. "Users now have a choice, and Microsoft needs to fight for their user base." And the fight must be different, as this shift will be unlike others Microsoft's managed. "With tablets, there's a fundamental shift of behavior happening."
That shift, more toward content consumption with less emphasis on the creation that's been the domain of PCs, has been fueled by vibrant app ecosystems, a wide range of device form factors and prices, and an attention to ease of use. All which Microsoft arguably has yet to show it can pull off.
"I'm very concerned about how they're going to dig themselves out of this hole," added Gillett. "They've made major changes before -- Bill Gates' call on the Internet, for example -- but they've never had to do it under this kind of pressure. They were once in a dominating position, but what works when you have 90% of the market doesn't work when you have 30%."