Automatic Updates on Windows Servers (or, “Why I am Certifiably Insane”)

I want to make a confession. I am violating one of the most central, most critical, most well-known commandments of systems administration.

I am letting my Windows Servers auto-update.

Not just download updates and ask me to install, either. Full on, straight from the Microsoft marching orders auto-updating. Reboots and everything.

So, am I insane? Probably, but here’s the thing: I work for a small municipal government. My organization can tolerate downtime, especially at 2:30AM when nobody’s watching (if a server goes down at the water park and nobody is around to see it, did it really go down?). There’s no financial impact of a file server rebooting itself to install a security update. If anything, it’s a benefit — we all saw what happened to the folks in Atlanta this year — and I think we need to do it more often.

More Sysadmins and IT Managers need to take a hard look at the systems they oversee and make some of these tough decisions (and let’s be honest, deciding to let a server that might not be redundant reboot itself for MS updates is the tough choice — letting it just go on forever without updates is the easy way out), and more importantly, they need to be prepared to make a stand when Management comes knocking to ask why there were a few minutes of downtime. We need to stop buckling to business or management pressure when it comes to security. Full stop.

I know, I know — it’s easier said than done. People could lose their jobs for defending that kind of decision making, and we all know that Microsoft updates haven’t exactly been the shining example of Quality Control lately… but when you’ve got Windows Server 2003 installs still running because “nobody wants to deal with the downtime from the upgrade”, you’re setting yourself up to get fired anyways when the shit hits the fan and you get hacked, or something just stops working and there’s nothing you can do about it because it’s not supported. If you never say anything, management can use that as an example of incompetence, so… you might as well take your chances and say something.