Monday, August 5, 2024

Secure Apps Take a Village


I reflect on recent experiences and the tension between rolling out features and ensuring the product is secure. Features are flashy. They make good keynotes and/or demos. Features get customers excited and make money.

Security is about the backend. It's not flashy. It's hard to demo security; you probably wouldn't want to even if you could. But when something goes sideways, a security issue will lose you customers. It's like giving your competition bullets—"Hey, did you hear about that security breach at Acme?"

Security is getting more complex and more challenging to do well. Sure, we are smarter and better understand vulnerabilities. However, applications are also becoming more complicated (e.g., log4j and versioning). Complexity makes security harder—it just does. The bad actors are as determined as ever, and their methods continue to evolve.

I attribute much of this tension to the organization's culture. A typical culture pattern is when leadership compresses engineering estimates, and as time runs out, security verification takes place. This leads to pressure to complete verification and remedy errors without impacting the date. Regardless of the number of times that leaders tell people how important security is - actions speak louder. We must ship at this point in the project, leaving uncomfortable conversations and hard choices. 

The tension between shipping and being secure starts early, when most of the time is spent discussing/planning customer-facing features. Sure, security comes up, but in my experience, it gets a different in-depth consideration. If we are lucky,  the challenging security conversations/decisions are before we launch - and not after. Talking about security feels more like a bad thing when it's this late. Further contributing to this tension is when leaders push to make a date, a security issue is identified, and in response, they make statements akin to - "Security is always a priority, so when I push on the date, my expectation is that the system is still secure."

Imagine a product where this culture goes on for a long time; the product is very successful and lucky that lurking security issues are private. With some certainty, this culture will catch up with you, and a critical mass of security issues will arise, requiring engineering resources. Sometimes, the number and/or severity of the problems is so great - that feature delivery is paused, and most of the team is focused on remediation. I bet that for every case like this in the press, many more are not public.

Too often, I have seen teams rely on the hero model: people who, early on, take the risk of spending time on security—which, in my opinion, is under-acknowledged/appreciated. Or the heroes who scramble to fix issues after they are found—typically in a severe time crunch. The hero model is not sustainable and is unreliable for ensuring secure systems. Further, the hero model is often a symptom of something "wrong."

So, let's stop relying on heroes, best intentions, hollow statements, and punishing the bearers of bad news. In a fiercely competitive world, features are prioritized, and security often gets less attention, sometimes even becoming an afterthought. This is a culture war that needs to be waged. 

We must start by considering security not just as a necessity but as a feature as important as any other. We need to talk about it early. We need to do security reviews early and often. For instance, start a threat model on the first day, keep it up to date, and assess design decisions in the context of how it would change the threat model. Activities like this involve staffing security-oriented teams and embedding them into the project teams. Then, empower them to ensure positive security-oriented outcomes. A culture of security is independent of volunteers who take on additional responsibility to ensure a secure system.  We need mechanisms to help people do the "right" thing. Then, acknowledge (early) security wins, such as actions to avoid an event.

A culture of security is hard to change, and as leaders, we need to be honest with ourselves about it — are we backing up our words in ways that will lead to the outcome we want? Look in the mirror. Yes, the words mean something, but it takes more than words.

PS: If you're unfamiliar with the African phrase "it takes a village" - see here.

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