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Windows 10 issues continue with Autopilot update

Microsoft recently rolled out a Windows 10 update to general users that was intended only for Autopilot-configured machines. After past issues, are users comfortable with Windows OS updates?

Although the latest issue with a Windows 10 update does not appear to have caused damage, users spoke of the need for further testing and oversight as Microsoft rolls out new versions of its OS.

Last week, Microsoft issued an update intended solely for Windows Autopilot-configured computers to the general public. Autopilot is a way for enterprises to automatically set up and configure new devices.

In its notes about the release, Microsoft indicated that the update should have no effect on users who don't use Autopilot. Still, users offered mixed reactions to the news -- especially given that past updates have caused Windows 10 issues such as data deletion, device freezing and the re-lettering of a computer's drives.

William Warren, the owner of Brunswick, Maryland-based IT services company Emmanuel Technology Consulting, said he was concerned about continuing issues with Windows updates.

"They just can't seem to get it right," he said. "When you're talking about an install base as diverse as [the one] Windows has to deal with, I don't expect things to be totally problem-free but, with something like this, it's like, 'C'mon guys, pay attention.'"

William WarrenWilliam Warren

Warren said he had been keeping his clients on an older version of Windows 10 and would likely have them stay there until required to update.

"At least with this one, it didn't become a huge data destruction debacle," he said, referring to an October 2018 patch that deleted files of users who work with Known Folder redirection.

How software is currently developed is the real culprit, according to Warren said. He referred to across-the-board issues with software, including the flawed Boeing 737 Max software that led to plane crashes.

"What people need to do is stop fast iteration," he said. "They need a second, third or fourth pair of eyes looking at code before it's out the door. The mindset now is to fix bugs after release."

With such a model, Warren said, companies treat customers as beta testers -- or, in some cases, alpha testers.

"The file deletion debacle never should've gotten past QA," he said, adding that he believed Microsoft had curtailed its use of testers in favor of having insiders find problems. "It's Microsoft being tone-deaf."

He did note that the latest problem did not seem to cause major issues.

"With this one, I see it as someone who didn't tick a box they should have, or did tick a box they shouldn't have," he said. "It could have been a lot worse."

Daniel BeatoDaniel Beato

Daniel Beato, director of technology at New Jersey IT consulting firm TNTMAX, said he hadn't used Windows Autopilot and hadn't been affected by the recent update. Still, he noted a lack of consistency with Microsoft's rollouts.

"I think there needs to be more testing," he said.

Beato said there seemed to be fewer Windows 10 issues with updates over time, although minor snags, like losing Google Chrome extensions after updating, remained.

"There were not a lot of big problems, and not a lot of problems with applications," he said. "They have done a little better."

Beato said, although the latest problem seems to be an oversight, it's important to recognize that everyone can make mistakes.

"There's a human part of things that, I think, sometimes we forget," he said.

Automation tech continues to mature

Mark BowkerMark Bowker

Mark Bowker, a senior analyst at Enterprise Strategy Group, said the tension between updating software and maintaining stability was an old one, although one that has heightened in recent years.

"Updates have always been a thorn in the side of IT pros, given their responsibility for deploying and maintaining them," he said. "Five years ago, the cadence was much further apart. Now, it's coming at a much faster pace, and it has some IT pros thrown."

Updates, Bowker said, can bring two things: broken applications or an improved user experience.

Andrew HewittAndrew Hewitt

As far as Autopilot goes, Forrester Research analyst Andrew Hewitt said he believed users would still have confidence in that service.

"There's widespread belief that these new deployment automation technologies are still fairly new. They are going to have their bugs and issues and still require a fair amount of work to get them up and running," he said. "I expect this space to mature rapidly over the next one to two years as customers find ways to optimize the service and Microsoft continues to mature [it]."

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Modern software development relies on an iterative model, but is Microsoft putting too much emphasis on it with Windows 10 updates?
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