OSOT Windows Update

[lvredrider]

I've run into an issue with a Windows 2016 standard gold image, in trying to run Windows update, I launch OSOT, enable updates and when I try to check for updates, the button is grayed out. Web search solutions ( which are more general in nature) haven't helped, things like delete this reg key, run that thing and do this and it's fixed, well those suggestions aren't working.  Not sure it's an OSOT issue or not but my Win 10 images don't have this issue, and I was able to update this server image last month and did not have this issue.

Again, this is a fairly standard fully optimized (using OSOT) Win 2016 Server Standard v 1607, is not joined to a domain (so no GPO applies), I really don't want to build a brand new image. Anyone else run into this or a similar issue?

[lvredrider]

I guess I am the only one who has come across this issue. Strange

My fix: deploy a new image and start over.

[almostIT]

Nah, same issues. Every time I try to update Windows with the OSOT tools it doesn't work. It just breaks Windows Updates. I've tried the most recent version of the OSOT tool and still does the same thing.

[almostIT]

Try this: https://virtuallyunboxed.wordpress.com/2019/11/14/windows-updates-and-osot/

The script I attached (it's a PowerShell script in Text format, just convert to .ps1) does what is described in this post, but "automatically". Hope it works for you, it worked for me. 

[lvredrider]

Thanks, oddly enough the problem seems to come and go, sometimes it's there sometimes I can update without issues.

My team has been testing various automated tooling and it looks like we'll be using a combination of Packer, Ansible and Terraform and completely automate all of this. IaC all the way. Pull the trigger and a new already optimized VM is provisioned and deployed in minutes. The less I have to touch anything the better!