Windows Update with PowerShell

We generally connect to backend servers via a jump-box or bastion host. On Windows this means RDP into the jump-box, then RDP from the jump-box to the backend server. However, recently a Windows update meant that the jump-box (which had the update) couldn’t RDP to the backend server (which hadn’t got the update). No RDP => no access to update the VM to restore RDP. Lots of fun!

In that case I managed to use Remmina from a Linux box to access the backend directly; however since we are going to hit this issue again we needed a better fix.

Cue PowerShell; this is deployed via Octopus so will work when RDP doesn’t. As an additional perk it means updating becomes much easier.
Continue reading