This is going to be a contentious one, but here at Anchor we think automatically applying updates to servers is a Good Thing. It’s definitely not for everyone, but in an environment like ours with hundreds of managed servers it’s the only way you’re going to get things done and get any sleep at night.

Sysadmin of note Tom Limoncelli advocates rolling out updates to progressively more machines with prior testing beforehand to mitigate the scope of potential problems (it’s called “one, some, many”). It’s certainly a good strategy for a large number of homogenous computers, but what we’re talking about here is a bit smaller-scale.

Specifically, we have customers with servers that we never touch, we call this Anchor Monitor. These customers often have particular environments that they’re better off supporting themselves, so we monitor the machine to ensure it’s still on the network, and leave it at that. Unfortunately they’re not always kept up to date, so one of the more recent improvements to our process has been to enable automatic updating by default – it’s up to the customer if they want to change this once it’s handed over to them.

We’ve written this into a short procedure if you’re interested. It applies directly to Debian and Redhat distributions, but it’s easily portable to other systems. If you run Windows, it’ll already be hassling you every 20min for updates.

If you’re one of our dedicated server customers, you’ve got the option of a paid support package, the choices being Anchor Secure and Anchor Complete. Whatever you choose (or if you decide you don’t need one), we just hope it’s the right one for you.

One of the services we provide with a support package is keeping your system up to date. For Linux machines this means installing updated packages as they’re released, and for Windows this means staying on top of Windows Update. We can do a lot of this without you ever noticing, but Windows Updates almost always require a reboot of the machine, which we schedule with our customers by email.

This brings us to an amusing little snippet from one of our customers.

Anchor: We’re going to reboot your server next Wednesday at about 11pm, please tell us if that’ll cause any problems.

Customer: Ah, I was not aware of Microsoft’s update schedule.

Great Lord almighty, there are undiscovered tribes in the Amazon that know that Microsoft releases patches on the second Tuesday of the month!