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Q: My issue is with Windows 10 Update Assistant. Every morning when I turn on the computer it displays the message “This PC is not running the latest and most secure version of Windows 10. This PC is running version 10240. The latest version is 16299. Click ‘update now’ to get started.” I let it do its thing which sometimes takes an hour, restart, and then I can finally do what I need to do on the computer. But the next morning, it does it all over again. I’m thinking there’s something blocking to where it doesn’t update, but I’ve tried everything to no avail. Even tried to turn off automatic update, but it has a mind of its own.

– Melba P.
Fort Walton Beach, Florida

A:  It sounds like you are one of the increasingly rare people that fully shut-down your computer at night.  I’m not necessarily saying that there’s anything wrong with that, especially if you have good reasons for doing so.  Whatever those reasons are, I can probably give you far better ones for leaving it powered up, but like so many things, it comes down to a matter of personal choice.  I will say that the entire Windows Update process seems to revolve around getting updates done when it doesn’t interfere with the use of the computer.  The natural target for that is the middle of the night, when most people are sleeping.

Your assumption that the update is failing might be absolutely correct.  However, before we assume that, I’d like to point out that in most cases where an update doesn’t succeed, it fails with an explanative error message on the screen, which often requires an advanced degree in Computer Science to interpret and understand.  In your case, the only error you’ve mentioned is one you receive upon booting your computer.

During my research into your problem I made a rather interesting discovery.  It seems people running the Windows 10 Fall Creators Update may have issues when updating their PC (Thanks, Bill!)  There are actually two problems. First, the installation might stop at 99% and start to show excessive CPU utilization.  This requires the PC to be forcibly restarted.  In the second problem, the PC reports that an update has failed but Microsoft claims that the update actually succeeded and it is the error message itself that is at fault (Thanks again, Bill!)  It sounds like it’s possible that the second scenario could be what’s happening with you, Melba, although I’d feel more confident in my analysis if you had said that there was an error message associated with the failed update.

At this point, you may be uncertain just exactly which version your PC is actually running.  To clear things up, you can always examine Windows itself and see the version information.  Click the Start button, then the Gear icon, which is the “Settings” button.  In the “Find a setting” box, type the word ‘about’ and select “About Your PC” from the displayed choices.  Scroll down to the section that says “Windows specifications” and there you’ll find the OS Build number, which, as your error message said, is supposed to be 16299.xxx if you want the latest. 

From this same box you can also see if there are updates waiting.  In the Windows Update dialog, there is a button labeled “Check for Updates.”  This button does exactly what it says, and will go out to the Windows Update Server and see if there are any new patches or feature updates that have not been installed.  In your case, if there is an update that is regularly failing to install, it will be shown here as still pending.

If the update is actually failing, you can get more information by viewing your system’s update history.  Again, click Start->Gear Icon, and this time type ‘Update history’ in the box, and select “View your update history”.  If you find failed updates, first make sure they didn’t succeed on a subsequent attempt.  Barring that, to get more information click on the name of the update, and it will take you to a Microsoft web page that describes the update, any known problems with it, and any subsequent patches that have been made.