There's never a good time to be complacent about Windows updates.  And if there was, now wouldn't be it.  With malware threats at an all-time high, and password-stealers such as GameOverZeus threatening to make a comback, it's important that your computer remains fully patched.

Whether you do this manually or automatically is entirely up to you.  For most people, the automatic option is the simplest.  Just turn on automatic Windows updates and the computer will take care of the rest.

Or will it?  How can you be sure that the updates really are being downloaded and installed?

Once in a while, it's a good idea to check.  From your control panel in Windows 7 and below, go to Windows Update and then click to view the list of installed updates.  If you're using Windows 8, click on the Settings charm, then click Change PC Settings, then click on Update & Recovery.  Either way, you should end up at a list of updates that your PC downloaded, so you can check that there are some recent entries in there.  You should also check the "status" column to ensure that all of the updates installed correctly.  

As you can see from the screen shot below, this isn't always the case.  Here, lots of recent updates have failed to install.

Tracking down the cause of a failed update isn't always straightforward.  Start by googling words such as "failed to install", along with the KB number of the update (which you'll find listed in the report as shown below).  If your update history shows some error codes, search for those too.  It's not always an easy task, but is nevertheless an important one.  It's a good idea to set aside some time every few months to ensure that your computer is as up-to-date as you think it should be.