After complaints from both consumer and enterprise users of Windows 8.1, Microsoft extended the deadline, but upset customers still felt like Microsoft twisted their arm to get them to move quickly to the 8.1 Update.
To make matters more confusing and bothersome for Windows 8.1 users, Microsoft allowed those who had stayed on Windows 8 to continue to receive all security and non-security updates through January 2016.
Microsoft also needs to do a better job of keeping enterprise customers informed about the future roadmap for Windows, according to Gillen. "They haven't been clear on that with Windows 8," he said. "Enterprises need directional information from Microsoft on how the product will look like in the future."
A promising effort that could help Microsoft with its business customers is the push to unify the Windows code base and APIs, so that it will be easier for Windows commercial and enterprise developers to create tools, applications and integrations for the OS.
In April at its Build conference, Microsoft announced the ability to create "universal" applications that can run on Windows, Windows Phone and the Xbox via the new Windows Runtime architecture using Visual Studio 2013 with Update 2 or later. Developers can modify the applications for specific devices, but they don't have to write them from scratch in each case.
However, there is more to come on this effort. In late July, during Microsoft's fourth fiscal quarter earnings call, CEO Satya Nadella said that the next major version of Windows would be a "single, converged" OS for "screens of all sizes."
"We will unify our stores, commerce and developer platforms to drive a more coherent user experience and a broader developer opportunity," he said then.
An open question is what Microsoft plans to do with Windows RT, the Windows 8 version for devices that run on ARM chips. Some industry observers have speculated that Microsoft will not maintain Windows Phone and Windows RT as separate OSes.
Windows Phone had a 2.5 percent share of the smartphone OS market in 2014's second quarter, down from 3.4 percent a year prior, according to IDC. Meanwhile, Windows had a 2.1 percent share of the tablet OS market at the end of 2013, according to Gartner.
These figures show how dramatically Microsoft has failed in the past two years in its attempts to improve its position in the smartphone and tablet OS markets, which had been the main mission of Windows 8 and Windows Phone 8.
With Windows 9, Microsoft will try again to better compete against iOS and Android, while at the same time protecting the dominance it still holds of the PC OS market. And it can't afford another Windows 8-like blunder.
"Windows 9 has to be a watershed release for Microsoft to stay in the game," Silver said.
Adds Gillen: "Microsoft needs to get this one right."
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