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Q: For the past 8 or 10 days, I’ve been getting a popup in the lower right of the screen which tells me there is a Windows update and I should click on either “restart now,” or “remind me tomorrow.” I first clicked on “restart now”. I later received another popup that said the system was busy when I tried the update so it could not take action. the next time I first made sure nothing was running and then did the restart with the same result. I am now clicking on “remind me tomorrow” when it appears. In addition, two more options have appeared in the “Start” menu, they are: “Update and shutdown” and “Update and restart”. Any ideas? I don’t know how to capture the popups because they go away pretty quickly.

– Don K.
Shalimar, Florida

A:  The first thing that comes to mind, Don, is to wonder if you’re dealing with more than one update.  If the system needs to be restarted, it generally occurs after an update takes place – not before.  I discussed the reason for this at length in a recent column.  The short version is that certain files that need to be updated are locked open by the operating system while it is running, and the only way to access them is to do so either while the system is shutting down, or before the boot process progresses to the point where the files are once again locked.

Now, having said all that, one important thing to know is that not all updates require a restart.  Those that do require one cause the behavior you described.  So, the reason that I mention all of the above is so you understand that Windows is asking you to either restart now, or be reminded later, because it has an update to perform (possibly more than one) that it knows is going to require a restart.

So, you said you clicked “Restart Now” but you didn’t say whether the system actually restarted.  When it says “Now” it means exactly that.  So, if you continued working, or if the system did not immediately go into shutdown mode, something else was happening on the system that prevented the system from shutting down as planned.  This can happen when certain high-priority processes are running, or for something as mundane as a program such as Microsoft Word prompting whether you want to save your current file before exiting.  If such a dialog is left on the screen, there is a good possibility that Windows won’t shut down, because it is actually attempting to prevent you from losing your work.  If this happened, or if something else prevented Windows from shutting down, you would indeed get a message that the system was busy when it tried.

So, you went on to say that you did the restart, and got the same result.  Again, I would question whether you’re certain you’re dealing with a single update and not several; each of which requires a restart (this is a rarity, but it does happen).

Have you tried either or both of the other options that you mentioned that appeared in your menu?  Their presence confirms that the update(s) in question cannot be performed while the system is running, and must be systematically applied during a reboot. 

Of course, it is always possible that this is not multiple updates, and instead is a single update that keeps failing each time you try to install it.  This happens occasionally (Thanks, Bill!).  Such updates may require elevated privileges to successfully install, or require a file path that’s not available on your machine due to a vendor-specific Windows installation.  If one of these situations is indeed happening, you can get more information by going into Windows Updates and looking at the Update History.  You get there by clicking Start->Settings, then select “Update & Security” and then “Advanced options” and “View your update history”.  The list contains all the successful and failed attempts at performing updates, and should give you more information on why a given update failed.

As for capturing the failure dialogs, you only need to be quick enough to hit a single key in order to capture them.  I covered methods of grabbing the contents of the screen in Issue #503 and Issue #540, both of which can be found in the column archives over on ItsGeekToMe.co.