Suffering through Windows Update

Why should I have to worry about whether it’s safe to update my Windows PCs?

Microsoft Windows update cycle arrows with overlay a laptop and mobile phone.
Microsoft / IDG

I use a lot of different desktop operating systems — Chrome OS, Linux, macOS and Windows — but there’s only one of them that worries me every time I upgrade it. That troublesome OS? Windows.

Remember when people used to say that they couldn’t use desktop Linux because it didn’t support their printer, graphics card or scanner? Ha! With the Windows 10 May 2019 Update, Version 1903, Microsoft came right out and warned us it might not install on our PCs if we use external USB drives or SD cards.

Not all my Windows 10 computers have external USB drives. Only all my desktop PCs.

Guys! Where’s your quality assurance? Lately, Microsoft has been tripping over its Windows upgrades every few months. Remember the Windows 10 October 2018 Update, which erased files? I sure do.

This time around the problem was with “inappropriate drive reassignment.” So, for a while, if your computers had any such storage attached they were “blocked from receiving the May 2019 Update.”

Of course, you could work around this by removing your drives or SD cards. But you know what? It’s not my job to make sure my machine works with Microsoft’s “upgrade.” It’s Microsoft’s job.

I also can’t help but think that, while I knew about this problem, most people do not pay as much attention as I do to potential Microsoft patch problems. No, what most people do is just update without a lot of thought and with blind faith that all will be well. It’s a misplaced faith. Trusting in Microsoft patches these days is not a smart move.

Now, after a delay of weeks, John Cable, Microsoft’s director of program management in the Windows delivery and servicing team, has announced, “The May 2019 Update is available for customers who would like to install the latest release.”

But don’t start installing it quite yet, buckaroos.

Cable also said that “IT administrators should begin targeted deployments to validate that the apps, devices and infrastructure used by their organizations work as expected with the new release and features.”

In other words, there may still be bugs here. I’m shocked — shocked, I tell you — to see this.

To keep unpleasant surprises to a minimum, Microsoft now has a new Windows release health dashboard. This provides timely information on the current rollout status and known issues (open and resolved) across both feature and monthly updates.

That’s a really welcome improvement. With this you can much more easily find issues and fixes for all currently supported versions of Windows. You can also search for problems by keyword and check on the current status of known issues.

This is much better than the seek-and-hope-you-find approach we had to use before for finding Windows issues.

But, even here, there are problems. The dashboard isn’t being kept up to date. For example, as I write this, days after Microsoft said it’s now OK to manually update to the May 2019 update, the dashboard still states: “Microsoft is working on a resolution and estimate a solution will be available in late May.”


At this rate, I expect to upgrade my Windows 10 boxes to the May update in August. I recommend you take the same course with your Windows computers.


Copyright © 2019 IDG Communications, Inc.

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