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Microsoft Windows 10 October 2018 Update stumbles out of gate

The most recent Windows 10 update includes enhancements for business users, but it ran into major problems shortly after its release.

Microsoft's latest feature update for Windows 10 did not hit the ground running.

The Microsoft Windows 10 October 2018 Update became available on Oct. 3, and the company pulled the update just three days later, because users reported missing files after they updated. Microsoft this week released an updated version to Windows Insiders for further testing, but has yet to announce when it will be generally available again. The issue has shaken some experts' faith in Microsoft and the Windows update strategy.

"It's a step backwards in market confidence in Microsoft," said Doug Grosfield, president and CEO of Five Nines IT Solutions, a consultancy in Kitchener, Ont. "The message has been, 'Let's jump into Windows 10, because it's going to simplify your life, be more stable [and] more secure.' They have ground to recover."

What went wrong

The problem was a direct response to an issue with the April 2018 Update in which some users reported seeing empty duplicates of their Known Folders -- Desktop, Documents, Pictures, Screenshots and Camera Roll. The company added code to the Microsoft Windows 10 October 2018 Update to counteract this problem.

The code backfired, however, for users who work with Known Folder redirection, which redirects files from the default location of Known Folders to another folder. If files existed in both the default folder and the relocation one, the update deleted the default and all the files within it -- even those that weren't redirected. This problem occurred when the user redirected files to a different drive than where the Known Folders live or to Microsoft OneDrive.

"These issues should've been addressed before it was released," said David Aldarondo, manager of network services at Post University, a primarily online university based in Waterbury, Conn., which plans to finalize a Windows 10 migration in December. "I lose faith in the release when something happens at launch."

Microsoft should be a lot more aggressive about saying, 'Here's what happened, [and] here's what we're doing about it.
Doug Grosfieldpresident and CEO of Five Nines IT Solutions

Still, it did not affect a huge swath of users -- only one one-hundredth of 1% of users who downloaded the update, according to Microsoft. The actual number of affected users is not yet available. Microsoft is working to recover any files lost after the update, but cannot guarantee it can recover every one, the company said in a blog post.

"Don't panic," said Steve Brasen, analyst at Enterprise Management Associates in Boulder, Colo. "Folks think it's indiscriminately deleting files, and that was not the case. Microsoft stepped up right away and resolved it fairly quickly."

Others said the company's response was not good enough, however.

"The communication was awful and continues to be," Grosfield said. "Microsoft should be a lot more aggressive about saying, 'Here's what happened, [and] here's what we're doing about it and when,' so we have some idea of the impact and the timing."

Windows Insider feedback approach fails

With Windows Insider Program for Business, IT can deploy preview builds of Windows 10 updates and gather feedback, then use the Feedback Hub to relay problems to Microsoft. During the Windows Insider preview for the Microsoft Windows 10 October 2018 Update, users reported the missing file problem, but Microsoft did not act on it, because it did not receive enough complaints.

"You'd hope that they're taking that feedback and taking it seriously," Aldarondo said. "It's unfortunate they're not, but it's a hard lesson learned."

To prevent major problems from slipping through the cracks in the future, Microsoft this week added a feature to the Windows Insider Feedback Hub that allows the submitter to designate the severity of an issue and the damages of its effect.  

"They'll get it right going forward," Aldarondo said. "I hope they learn from this."

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How can Microsoft prevent a repeat of the hiccup it experienced with the release of the October 2018 Update?
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