Microsoft slates skip-Windows 10 1809 upgrades for late June

This marks the first time the company has jumped past a Windows 10 feature upgrade as it moves to put last fall's update debacle in the rear-view mirror.

hand at keyboard with Windows logo
Thinkstock/Microsoft

Microsoft will start the process of skipping the problem-plagued fall 2018 feature upgrade late next month when it begins pushing Windows 10 May 2019 Update to PCs running version 1803.

The Redmond, Wash. developer has never jumped past one of its Window 10 feature upgrades.

"The Windows 10 April 2018 Update will reach end of service on November 12, 2019, for Home and Pro editions," Microsoft said in support document last week. "We will begin updating devices running the April 2018 Update and earlier versions of Windows 10 in late June 2019 to help ensure that we keep these devices in a serviced, secure state (emphasis added)."

1809's disaster led to upgrade regime change

Microsoft's announcement that it would soon upgrade Windows 10 PCs to the latest version would not have been out of the ordinary prior to last week. Twice a year since 2017, the company has refreshed the OS with new code that added features and improved and enhanced existing ones.

Then came Windows 10 October 2018 Update, aka 1809, the latter the numeric label in Microsoft's yymm format. That upgrade, which first appeared Oct. 1, 2018, harbored a known-yet-overlooked bug that destroyed user data. Within days, Microsoft pulled 1809 for retesting. It wasn't until mid-January - three months later - that Microsoft again began to distribute the upgrade, albeit so cautiously that within weeks the company gave up on getting the new version to users because the next in line, version 1903, fast approached.

Near the end of April, analytics vendor AdDuplex reported, Windows 10 1809 had been installed on fewer than 30% of unmanaged Windows 10 PCs.

Earlier that month, Microsoft had announced it would upend its Windows 10 update regime for Windows 10 Home (and portions of Windows 10 Pro). Rather than force consumers to accept each feature upgrade on the company's terms - Microsoft decided when each device was told to download and install a refresh - engineers would add "Download and install now" to this spring's 1903, as well as refit 1803 and 1809 with the option.

With "Download and install now," users can choose when to migrate from one version of Windows 10 Home to another. It also lets users decide whether to install a specific feature upgrade. If one does not apply the option by clicking on it in the Windows Update settings pane, the current feature upgrade is not to be automatically downloaded and installed on the PC.

The gist of "Download and install now" was that Windows 10 Home users could, for the first time, skip a feature upgrade by simply doing nothing. For example, with "Download and install now," those running 1803 - the April 2018 Update that began rollout on April 30, 2018 - would be able to bypass the troubled 1809 by not choosing the option. (Under the previous rules, Windows 10 Home users would have been forced to upgrade to 1809 before later moving to 1903.)

Microsoft wouldn't let people run a Windows 10 version indefinitely - that would have been a bridge much too far - but only when the current feature upgrade neared end of support date would Microsoft intervene, the company said in April. What wasn't clear was when that trigger point would come.

Now users know.

When Microsoft regains control

"For Windows 10 devices that are at, or within several months of reaching, end of service, Windows Update will automatically initiate a feature update," explained John Cable, director of program management, in a post to a company blog. "Starting this June, we will begin updating devices running the April 2018 Update, and earlier versions of Windows 10. We are starting this ... rollout process several months in advance of the end of service date to provide adequate time for a smooth update process."

Win 10 figure 1 download and install now IDG/Gregg Keizer

Microsoft will use its end-of-support exemption to "Download and install now" to upgrade PCs running last year's 1803 to this year's 1903, skipping the problematic 1809.

Windows 10 1803 is slated to exit support Nov. 12; a late-June beginning to the Microsoft-controlled migration to 1903 means that the company will have just under five months to shift the approximately 63% of Windows 10 Home users on 1803 (according to AdDuplex).

Whether by plan or through 1809's misfortune, Microsoft has navigated through its perpetually mutating upgrade policies to arrive at a result many experts have long urged the company to seek: Annual Windows 10 feature upgrades.

If "Download and install now" works as Microsoft has implied, users of unmanaged PCs - those running Windows 10 Home as well as Windows 10 Pro not monitored by an organization's IT or set by its user to defer updates - will upgrade once a year under Microsoft's direction, as Figure 2 illustrates.

Win 10 figure 2 download and install now IDG/Gregg Keizer

If Windows 10 Home users now running 1803 do nothing, Microsoft should upgrade their PCs to 1903 this summer and fall, then follow with an upgrade from 1903 to 2003 (the feature update, not the year) starting in mid-2020.

Assuming AdDuplex's numbers are accurate, even in the most general terms, a broad majority of Windows 10 Home PCs - and an unknown portion of Windows 10 Pro systems - will be on an annual upgrade tempo. In that, they'll join enterprises, who since September have been able to easily slow to an annual pace thanks to longer support lifecycles for xx09 feature upgrades.

But what of those running 1809 on Windows 10 Home and Pro? What happens to them?

Computerworld doesn't know. Microsoft won't be immediately upgrading them without user approval, a fact implied in its statement that it would do so for the April 2018 and earlier refreshes.

Users can, of course, click on the "Download and install now" option when it shows up in Windows Update to board the annual-upgrade train. (Although Microsoft issued cumulative updates for Windows 10 1803 and 1809 that included the option, those updates were only available to users who actively sought them; Microsoft will automatically shove those updates to all users on June 11.) That presumes they hear about the option, then find the option, unlikely in many cases since people have been trained, more or less, to wait for updates and upgrades to arrive, not go looking for them.

Microsoft may not mind. If a third of the unmanaged-PC base isn't on the every-spring upgrade track, so much the better to balance the load by keeping that group on the every-fall cadence.

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Copyright © 2019 IDG Communications, Inc.

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