What if your patch management solution fails to install certain updates? The answer: WinRM and PSWindows powershell module to the rescue. You can manually install it from powershellgallery.com or within a powershell prompt:

Install-Module -Name PSWindowsUpdate -Force
To remotely connect to a machine, you will need WinRM configured. After issuing the command Get-WindowsUpdate -ComputerName <PC> you will see the list of available patches. In the screenshot below, you can see the machine and various patches available to download/install. In this instance, my patch management software had issues deploying ‘KB5066835’. Note: The Size “89GB” is a glitch and is incorrect. That can be ignored.

I’m going to deploy it with powershell. To do this I will issue:

After issuing this command it creates a scheduled task as seen in the screen shot below and after some time the machine will install the missing patch and reboot.

If you run into issues remotely patching machines you may need to look at your WSMan trusted hosts and adjust it to the computer name you’re remoting to.
