Holy cow it’s been a while!  Real life must be catching up with me or something, I am not sure.  Anywho, I’ve had this issue where I have never felt comfortable automating Windows Updates on my servers in case the worst should happen.  Seems like a reasonable concern right?  Well I finally got over it, did some digging, and found a suitable solution that I am comfortable with.

It really is quite simple.  I hijacked some PowerShell modules from Technet Script Center (found here) and then did some work with the PowerCLI module from VMware to take a snapshot prior to the updates.  Once it is done taking a snapshot of a VM (I pull them from an array) it will begin updates, and restart as needed.  I do not delete the snapshots in an automated fashion at this time, I just check everything is still good when I get in the office in the morning and then remove them all with PowerCLI (assuming there is no issues) as seen below:

Since I said I run this while I’m sleeping, I obviously just have it set up with Task Scheduler running with a service account I created with access to all the necessary servers and my vCenter environment.  Without further ado, I give you what I have coined “UpdateAutoPilot” below: