stand in the gap

Gunnar Peterson has a great post: “Who Manages App Gateways? Who Indeed? Yo La Tengo – Call in Security DevOps”. I’m going to dive into the 2 basic problems Gunnar has touched on, and also move a bit further overall. (Warning: I use slightly different terms than Gunnar, so App Gateway is analogous to WAF to me.)

1. The basic question is: Who manages the app gateways? Or, who manages the Web-App Firewall? Netops plugs the hardware in and makes sure it talks on the right networks in the right directions. Sysops makes sure it talks in a way that it can interoperate with the systems it need to and gets monitored for health. Then what? In my opinion, this is as far as most organizations who check the box for, “We have a WAF!” go. They set it up, get it successfully in the middle, and then no one has the chops to actually tune and configure the thing beyond crossing their fingers, turning on the defaults, and breathing easy when it doesn’t break anything (all the while, it’s not really doing anything except the barest, most ridiculous attacks like a 1000-character URL request).

I do think Gunnar trivializes this just a bit by comparing these middle-of-the-ground tasks to Texas leaguers; this assumes that either side alone could solve the easy problem/catch the ball. I’d suggest that neither side *can* usually easily solve the problem, and actually requires someone in the middle, or someone on one side with many skills. It might be more like two outfielders playing so far away from each other, than a ball hit fast right between them requires a huge burst of inhuman speed for either of them to actually get under.

The point is, there are these gaps that security cares about, but traditional IT in anything but the smallest (and largest?) shops is not staffed to fill.

2. Security need to be cross-functional experts in a lot of shit. Gunnar totally covered this, so I really don’t need to, but it’s pretty much truth, despite my bias. I tend to illustrate this with the idea that coders are first taught how to copy one string to another. Then they’re taught more modern tricks on how to copy one string to another; the same simple concept, but with a few more tricks added on. Later on, they add the next layer of how to *securely* copy one string to another (if they’re lucky). Getting that far requires extensive knowledge and even experience. And that’s not even getting into being able to understand technologies outside the main one, such as DNS, server configurations, in-transit encryption, firewalls+in-transit communication needs.

Security is expected to understand code and the network and the server in such a way that they can configure very advanced technologies such as a WAF. And it’s not just understanding general code, but understanding the *specific apps* being protected.

I personally measure my opinion of developers based on how they understand those last few things. If they repeatedly just don’t get it, they’re just coders to me. (They might be really good, but they’re one-trick ponies.) But if they understand DNS, server configuration, and firewalls, at least to a general extend of knowing what matters to them, I deeply appreciate it. Those are your potential rock stars. Likewise, I adore sysadmins who understand code and can do cross-functional things like deep-dive into code traces on the servers and tackle memory leaks.

Or either of the above who have security skills and knowledge!

3. I think this lack of cross-functional understanding is another pressure on why the “cloud” (when it is just external hosting rebranded), has gained momentum. Developers have long made overtures to get administrative access to the servers that run their code, and hopefully sysadmins have rebuffed those overtures to do the server work on behalf of the developers. Have you ever walked up to a server that for the last 2 years has been adminned by a developer? Chances are pretty damn good that it looks about as good as a server adminned by a 14-year-old. That’s not a dig, really. If I tried to add code to your app, I’d fuck shit up pretty awful as well, and my code would be heinous. (This could be twisted around to say neither side will get better without being allowed to get experience with the tasks, but that sort of cross-functional short-term inefficiency does not fit anything beyond small business.)

In steps hosting and the cloud, where developers can drive those projects because it involves code, which netadmins/sysadmins don’t quite understand, and it might result in devs having administrative duties on these new servers. Which sounds great short term…