Usable security: the sudo security model

Edit: here’s the talk I was watching while writing this post, for context.

I’m starting writing this while I’m at Enigma 2016 listening to the usable security track. I think it’s a perfectly good time to start talk publicly about my experience trying to bring security to a Unix-based company I worked for before.

This is not a story of large company, the company I worked for was fairly small, with five people working in it at the time I was there. I’ll use “we” but I will point out that I’m no longer at that company and this is all in the past. I hope and expect the company to have improved their practices. When I joined the company, it was working on a new product, which meant we had a number of test servers running within the office and only one real “production” server for this running in a datacenter. In addition to the new product, a number of servers for a previous product were in production, and a couple of local testing servers for these.

While there was no gaping security hole for the company (otherwise I wouldn’t even be talking about it!) the security hygiene in the company was abysmal. We had an effective sysadmin at the office for the production server, and an external consultant to manage the network, but the root password (yes singular) of all devices was also known to the owner of the company, who also complained when I told them I wouldn’t share my password.

One of the few things that I wanted to set up there was a stronger authentication and stopping people from accessing everything with root privileges. For that stepping stone I ended up using, at least for the test servers (I never managed to put this into proper production), sudo.

We have all laughed at sudo make me a sandwich but the truth is that it’s still a better security mode than running as root, if used correctly. In particular, I did ask the boss what they wanted to run as root, and after getting rid of the need for root for a few actions that could be done unprivileged, I set up a whitelist of commands that their user could run without password. They were mostly happy not to have to login as root, but it was still not enough for me.

My follow-up ties to the start of this article, in particular the fact I started writing this while listening to Jon Oberheide. What I wanted to achieve was having an effective request for privilege escalation to root — that is, if someone were to actually find the post-it with the owner’s password they wouldn’t get access to root on any production system, even though they may be able to execute some (safe) routine tasks. At the time, my plan involved using Duo Security and a customized duo_unix so that a sudo request for any non-whitelisted command (including sudo -i) would require confirmation to the owner’s phone. Unfortunately at the time this hit two obstacles: the pull request with the code to handle PAM authentication for sudo was originally rejected (I’m not sure what the current state of that is, maybe it can be salvaged if it’s still not supported) and the owners didn’t want to pay for the Duo license – even just for the five of us, let alone providing it as a service to customers – even though my demo did have them quite happy about the idea of only ever needing their own password (or ssh key, but let’s not go there for now.)

This is just one of many things that were wrong in that company of course, but I think it shows a little bit that even in the system administration work, sometimes security and usability do go hand in hand, and a usable solution can make even a small company more secure.

And for those wondering, no I’m in no way affiliate with Duo, I just find it a good technology and I’m glad Dug pointed me at it a while back.

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