Windows Insider

Windows 10 Update Rules Change Like a Game of Calvinball

The "Calvin & Hobbes" cartoon's imaginary game of making the rules up as you go is a near-perfect representation of what modern IT has become.

• By Ed Bott
• 10/13/2017

Who's ready for some Calvinball? What, you've never played? The great cartoonist Bill Watterson invented the sport for his classic "Calvin & Hobbes" comic strip. It's a near-perfect representation of what modern IT has become.

In Calvinball, you make up the rules as you go. Rules can't be used twice (except, of course, for the rule about not using rules twice). You can wear, throw or bat using any equipment you like, so long as you're wearing a mask. And it doesn't matter if you start with an organized sport. "Sooner or later," says Calvin, "all our games turn into Calvinball."

Sound familiar?

I've begun to wonder lately whether Microsoft's product planners have taken up Calvinball. It sure feels that way when I look at the Windows Update for Business feature, which Microsoft announced a few months before Windows 10 shipped. IT pros were justifiably nervous over the move to cumulative, mandatory updates, and they wanted more control over how and when those feature and quality updates roll out to their users. Windows Update for Business was intended to be the answer.

But IT pros who chose to deploy Windows 10 early were probably not reassured much by what happened next. With each new feature update -- Microsoft has delivered four of them in just a little more than two years -- the Windows Update for Business rules changed. First, you could defer feature updates for eight months. Then it was 180 days, but that changed to 365 days with the next feature update. At some point, there was a two-month grace period, but I can't recall if it was ever formally acknowledged.

Eventually, even the names of the release channels associated with Windows Update for Business changed. For the first two years after the Windows 10 launch, Microsoft distinguished between the Current Branch (first public release of a new Windows 10 version) and the Current Branch for Business (roughly four months later). Now, those release channels go by much more awkward monikers: Semi-Annual Channel (Targeted) and Semi-Annual Channel.

At least I believe that's how it went -- those shifting settings begin to run together after a while. If you're also working with Insider Preview builds, just give up on trying to keep track of which rules are associated with each version.

How is a harried IT pro supposed to plan deployments and rollouts when the rules are constantly changing? That's a legitimate question to ask Microsoft, a company that built its reputation on backward compatibility. Learning how Windows works is just part of the job, but having to relearn core features every six months shouldn't be necessary.

This "change it with each update" approach also creates headaches for anyone developing documentation. A comprehensive how-to guide written in mid-2016 requires major revisions to remain relevant in late 2017. And by the time those revisions are complete, fully tested and ready to publish, a new update is out. That same phenomenon also makes it more difficult to sort through search results when you're looking for answers and explanations. Determining which results are relevant to the version you're using now can turn a simple search into a puzzle.

To Microsoft's credit, the company has been doing a much better job of organizing and updating its online technical documentation. The repository at docs.microsoft.com leads to thorough, frequently updated articles, with separate sites for software developers, device makers and IT pros.

So, is frequent change the new normal for Windows? It's possible that the flurry of activity around this feature is just part of the bumpiness associated with the initial takeoff of Windows 10. If that's the case, maybe the Windows Update for Business rules from version 1709 will stick around for versions 1803 and 1809.

But I certainly wouldn't count on it. After all, the only permanent rule in Calvinball is you can't play it the same way twice.