Hey there, Ferrariassassin.
Are you using an SSD or an HDD for you OS? Have you had any other issues, such as freezing/hanging of the system, unusual sounds/noises coming from the drive (if it's an HDD), unusual transfer speed, etc?
Basically you might have a ton of programs on startup, and all of these processes need to be closed before you're able to restart, which might lead to the issue at hand. Other than that, you should make a full scan with an antivirus program (with updated database) to see if the same thing happens. You should also try to update your OS if it has any updates available as this might be Windows related (caused by a service or something else).
If you are not 100% sure that your drive is healthy, I'd advise you to backup the important data and run some tests on it with its manufacturer's diagnostic tool, to see if anything alarming pops-up.
Please let me know how everything goes.
Boogieman_WD