Microsoft Fighting Previous Blunders With Windows 10 May 2019 Update Rollout

Microsoft is learning from the almost comical bungling of the Windows 10 October 2018 Update. The company announced today that rather than automatically updating compatible devices to the next major version of Windows 10, the Windows 10 May 2019 Update, it will give people the option to install the update or delay it until they’re confident it’s safe to use.

We’ve been over the Windows 10 October 2018 Update’s many problems over and over again. The short version is that many people weren’t prompted to install the update until January 2019 because it had so many issues Microsoft needed to fix. And not all of them had actually been addressed by the January rollout; that was just when Microsoft felt comfortable with releasing the update anyway. The company done goofed.

So now it’s switching things up. Microsoft said that for the Windows 10 May 2019 launch it will notify people that it’s available. If they want to install it right away, they can. If they don’t, they can hold off, and Microsoft said it will only install the update when a device is nearing its end of service because “keeping machines supported and receiving monthly updates is critical to device security and ecosystem health.”

Microsoft will also improve its update testing, it said in its blog post: 

“We are taking further steps to be confident in the quality of the May 2019 Update. We will increase the amount of time that the May 2019 Update spends in the Release Preview phase, and we will work closely with ecosystem partners during this phase to proactively obtain more early feedback about this release. This will give us additional signals to detect issues before broader deployment. We are also continuing to make significant new investments in machine learning (ML) technology to both detect high-impact issues efficiently at scale and further evolve how we intelligently select devices that will have a smooth update experience."

Microsoft followed its reassurances that the Windows 10 May 2019 Update’s rollout should be far better than its predecessor’s by announcing that Microsoft will push it to the Release Preview Ring of the Windows Insider Program next week. The company said it will “begin broader availability in late May” for commercial customers—as long as they opt in—and “customers whose devices are nearing the end of support on a given release.” It didn't provide a firm release date.

Microsoft also seems to recognize that people might not be ready to trust the Windows 10 May 2019 Update despite these precautions. So it’s planning to introduce a “new Windows release health dashboard later this month that will empower users with near real-time information on the current rollout status and known issues (open and resolved) across both feature and monthly updates.” It will also make it easier to find content—blog posts, updates, etc.—related to a given update.

The next major version of Windows 10 was originally expected to debut in April. That seemed unlikely after the Windows 10 October 2018’s prolonged rollout, though, so it’s no surprise that Microsoft has essentially delayed the update by a month (or two, considering Microsoft only mentioned business customers and end-of-support devices for the late May launch). It also shouldn’t be unwelcome—who isn’t willing to wait one month for an update that should, in theory, be more stable?

Microsoft has already been testing the following Windows 10 update with Skip Ahead members of the Windows Insider Program, so the push from April to May might not lead to a similar delay this fall. But we’ll see how this update goes before we start thinking Microsoft learned everything it needed to from the Windows 10 October 2018/January 2019 Update.