You already know that I am fast to apply updates and move to new products. I have almost all our WSUS updates set to auto approve and I load them on our servers and workstations the same day. I have a lot of faith and confidence in the patching process. But every once in a while, they bite back.
I can recall a few years ago that Microsoft got a lot of flack for blue screening computes with an update. I was keeping up to date with the situation from various news feeds. I unapproved the update while I investigated it more. We were not seeing any blue screens but other admins were. I saw all kinds of email flying around warning people and reporting issues.
As real details started to poor in, it turns out that the only computers that were blue screening were the ones with root kit infections. I immediately pushed that patch out to the rest of my computers. If my computers were infected, I wanted to know about it. In the end we had a clean bill of health but not everyone was so lucky.
I had the Bing desktop search bar get deployed once. Turns out I had feature packs on auto approve. I quickly fixed that and recalled it.
Last year Microsoft released a patch that would not trust 512bit certs anymore. I was following the progress of this issue for a while. The Flame malware was using a 512bit cert of Microsoft's that was weak enough to break. MS revoked that cert and later released this patch to break all 512 bit certs. I took a quick peek at our central IT's cert server. While I did see a few of those 512 bit certs, I saw many more 1024 and 2048 bit ones. I figured we had nothing to worry about.
Turns out that our email was using one of the weaker certs. So every one of my users was getting an error message that Outlook did not trust our email server. I got on the phone with central IT and pushed them to get an updated cert rolled out. They recommended that the rest of the org not install that patch. it turned out that they needed to update a root cert first and that is kind of a delicate process when you don't do it very often. That was not something they were going to put a rush job on. Luckily Microsoft had a KB that talked about this issue and offered a command that would trust 512bit certs again.
I was able to Powershell that command out to everyone and life returned to normal. I was able to revert that setting once the certs were taken care of.
The one update that almost bit us the hardest was the Powershell 3.0 and remote management update that was released around December 2012. We started to run into some strange issues with remote Powershell and SCCM config man. And before we knew it, we realized that we could not remotely Powershell anything. SCCM was also down and out. I started to deep dive into the internals of WinRM to fix this. Listeners were broken and Powershell was refusing to re-register settings it needed for remote management.
Something reminded me that Powershell 3.0 was out and I found it on our workstations. We started finding reports of compatibility issues with SCCM 2012 and Powershell 3.0. Config Manager was attempting to repair WMI but would corrupt it instead. We ended up pulling that patch using WSUS and everything returned to normal in a few days. The SCCM server took a little more work to correct.
Not having Powershell when you need it can be very scary. That is my go to tool to recover from most issues. So handy to for a WSUS check in or gpupdate or ipconfig /flushdns to resolve some issue.
I think patching fast works well in our environment because we have a good team that is flexible and quick to respond to these types of issues. We still get caught off guard from time to time, but we handle it well.
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