What to do when your automatic Windows Updates fail

Most people have their Windows Updates set on automatic. This means that when Microsoft issues a new “important” update, your computer dutifully downloads the update and installs it. Once the update is complete, a notification appears letting you know new updates were successfully installed.

But what if they aren’t successfully installed?

This recently happened to me and it was no picnic to fix. I started by ignoring the notification that the automatic updates failed. My hope was that my computer just experienced a hiccup in the update process which would correct itself the next time it tried.

Wrong. It failed again on the next attempt. And the next attempt after that.

One update leads to another

The problem with ignoring the failures is that every subsequent update from Microsoft “gets in line” behind the previous updates. So until update #1 installs correctly, update #2 will keep waiting its turn.

In other words, you need to fix the problem.

But like I said, the fix is no picnic. What you need to do is to install one update at a time. So instead of clicking the big, obvious Install updates button, you need to click the linked words 3 important updates are available. Of course, the number 3 will change depending on how many updates are ready to install.

Once you click the link, another window will appear with each update listed. Next to each update will be a checkbox. You’ll need to uncheck the box next to every update except for the one you want to install.

Your best bet is to pick the oldest update each time which should be the one at the top of the list. If all else fails, look at the number after the letters KB in parentheses after each description. The lower the number the older the update.

Be patient

Once you have your 1 update selected, click the OK button to proceed with the update. If your lucky, you won’t have to wait for your computer to reboot after each update. I wasn’t so lucky and had to reboot each time.

Don’t ask me why it works to do the updates one at a time and not all at once. That’s a question for the folks at Microsoft to answer. But at least you have a workaround you can use if this ever happens to you.