During that process, he discovered a deal breaker: His preferred security software isn't supported on Windows 8.1. He also flagged other compatibility problems. "I'm still in test mode," he said.
In addition to the Surface RT problem, other issues reported by customers and acknowledged by Microsoft include:
-- Windows 8.1 causes a variety of mouse-control problems for video games under certain circumstances.
-- Windows 8.1 can't complete its installation due to the presence on computers of certain outdated drivers or of incompatible software.
-- Some older PCs can't be updated from Windows 8 to 8.1 because the latter has some new hardware requirements.
Cherry pointed out that Microsoft is trying to speed things up on its end, aiming for a faster cadence of updates for Windows and other products, but that doesn't mean customers need to be in complete lockstep with the vendor.
"You need to have your own testing and procedures in place," Cherry said. That means doing hands-on testing, conducting research about the changes and contacting key hardware and software providers.
The Surface RT problem shows that Microsoft itself may be struggling with its own self-imposed faster pace of development. "Microsoft's testing needs to be up to the rapid release cadence," he said.
Ultimately, if Microsoft wants customers to have confidence in its products and in the accelerated update pace, it has to reduce the number of these situations.
"And when they occur, they have to be incredibly transparent about them: acknowledging them, providing workarounds and repairing them as quickly as possible," Cherry said, adding that offering detailed post-mortem accounts to customers is also important.
Sign up for CIO Asia eNewsletters.