On the airing of security grievances

I had a great day yesterday at DevOpsDays NYC. I gave a talk, but I also learned a lot from the other speakers and from the conversations. The format of DevOpsDays is half traditional conference with speakers, half “unconference” with open proposals of discussion topics and voting to establish which topics go where. They call it Open Space, and it’s a very effective way to let attendees explore the conversations they really want to have.

I proposed an Open Space topic on the “airing of grievances” around information security. What emerged was really interesting.

Attendees talked about companies that confused compliance and security, with disastrous results (hint: just because your auditor counts you compliant if you have a WAF with rules, doesn’t mean that those rules are actually protecting you from attack).

We talked about advances in declarative security, in which you could specify a policy for which ports should be open and closed via tools like Inspec.

We talked about the pains of trying to integrate legacy appsec tools into continuous integration pipelines (which happened to be the subject of my talk). I heard about people trying to integrate on-premise static analysis tools into their Jenkins toolchains when the application caused the scanner to exhaust all the memory on the machine. About on-premise dynamic scanners that run for eight hours. About the challenges of determining if an attack has successfully made it past a web application firewall.

And then Ben Zvan said (and I paraphrase), “We have a man-in-the-middle firewall (proxy) between our desktop network and the Internet that screws with security certificates, so I can’t use services that rely on certs for secure communication.”

And the floodgates opened. I talked about the secure mail gateway, intended to prevent phishing, that pre-fetches links in emails and thereby breaks one-time-use links intended for secure signup to new services. We talked about endpoint protection tools that can’t keep up with the MacOS update schedules, and thus make the user choose between taking the OS update and having the endpoint protection tool break, or not taking it and remaining at risk of exploitation of a dangerous newly-announced vulnerability.

The conclusion that we reached is that it’s a deadly dangerous irony that security tools actively stomp on security features, but it’s also the new reality. The complexity of the information security toolstack increases every year, with more and more vendors entering the space and CISOs being forced to become system integrators and figure out which tools conflict with which.

The lesson is clear: If security solution providers are serious about security, they need to build for reduced complexity.

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