Windows patching hell

A Unix sys admin struggling with patching Windows servers.

Never thought I’d end up babysitting MS Windows server patching and pulling my hair out as it takes an hour or more to install 100+ patches, reboot, 30 minutes “finalizing” the updates, declare it “failed” and 90 more minutes “reverting” the installs before rebooting again, wash, rinse repeat, until you successfully tell it which patch NOT to install.
I’m a Unix admin for Pete’s sake. There’s a reason I don’t (normally) do Windows. The only time a Linux server takes so long to boot is when it’s running on bare metal that takes 30 minutes to POST and/or it has lots of LUNs assigned and it takes a while to sort them all out.
I was hoping to have this 2008 server to a state that I could start installing the software it needs by the end of the day.

FINALLY it finished reverting and rebooting. Luckily it didn’t back out 100+ updates. The only one left to install is the one troublesome update that should be done last, because it causes this problem if you don’t.

Nope, spoke too soon. Had it re-check for updates and it now says ALL of the updates from the last go round still need to be installed. But now I see there’s a second update that partners with the known one, so hopefully de-selecting that one as well will fix the issue.

(And in another in a list of first that came with this job: never thought I’d be adding a new “Windows” sub-category under the System Administration category of this blog.)

1 thought on “Windows patching hell”

  1. Pingback: /dev/zero

Comments are closed.