Windows 10: Has Microsoft cleaned up its update mess? (Spoiler: no)

Four years after the debut of "Windows as a service," Microsoft continues to tweak the Windows Update for Business rules. And if you don't know how to play the game, you're likely to be surprised with unexpected updates.

Managing Windows 10 updates will always be a struggle for Microsoft Microsoft is overhauling how it delivers Windows 10 updates. But the almost infinite variation of PCs will make that an uphill struggle.

We are days away from the fourth anniversary of Windows 10's initial release, which also marks the beginning of the "Windows as a service" era. By this time, you'd think Microsoft would have settled on an easy-to-understand set of rules that IT pros can follow for managing updates.

Think again.

For 2019, Microsoft has changed the rules you painstakingly mastered last year. And if you're not paying attention, you could end up with a network full of update headaches.

Effective with version 1903, which is now rolling out via Windows Update, Microsoft is no longer supplying updates on separate channels for consumers and business customers. Instead, the initial public release goes to the Semi-Annual Channel, with no more Semi-Annual Channel (Targeted) option. (And even those names represented changes from the original November 2015 designation of Current Branch and Current Branch for Business.)

For anyone administering Windows 10 PCs in a business who used the older Windows Update for Business settings to manage feature updates, these latest changes require immediate action. On systems where the Branch Readiness Level is set to Semi-Annual Channel and no additional deferral is specified, Microsoft says your devices will begin updating to Windows 10, version 1903 in one week, on Tuesday, July 23, 2019.

Or at least that's when they'll be eligible to receive that update. Exactly when each device will receive the update is an AI-driven mystery.

Some devices, including Microsoft's top-of-the-line Surface Book 2 models that contain a discrete Nvidia GPU, are currently blocked from receiving the update automatically. (For details, see "Microsoft blocks major Windows 10 update for Surface Book 2 after bug makes GPU vanish.")

PCs that were previously blocked from updating because an external USB device or SD card was attached are no longer prevented from doing so, in a change that was documented just a few days ago.

For a list of other known issues with this and other updates, see the official Version 1903 Release Information page.

As I wrote in a column nearly two years ago, the ever-changing rules governing Windows Update for Business sometimes feel like a game of Calvinball, from Bill Watterson's classic "Calvin & Hobbes" comic strip. In Calvinball, you make up the rules as you go. And it doesn't matter if you start with an organized sport. "Sooner or later," says Calvin, "all our games turn into Calvinball."

Over the past four years, the deferral periods have changed, from eight months to 180 days and then to 365 days. There were two branches, which became two channels, and then became a single release period. Earlier this year, Microsoft formalized an 18-month support deadline for Windows 10, which trumps the deferral periods you might have set.

The only rule that matters for people who have to support PCs in business is simple: "No surprises." For large organizations that use central update management tools such as Windows Server Update Services or System Center Configuration Manager, that's possible. For everyone else, including the enormous population of PCs in small businesses, the only way to prevent unexpected updates is to manage the process aggressively.

That means setting deferral periods of roughly 180 days (to avoid being surprised when a Windows version reaches its end-of-support deadline) and then scheduling manual updates for a date shortly before the end of that deferral period.

When I wrote that Calvinball column, one Microsoft product manager told me I was being too harsh, that the company was simply responding to feedback from customers. Two years later, I think Calvin and I were right.