At the beginning of February 2017 I gave a brief talk that noted how Let’s Encrypt and cloud-based architectures encourage positive appsec behaviors. Over a span of barely three weeks, several security events seemed to undercut that thesis – Cloudbleed, SHAttered, S3 outage.

Coincidentally, those events also covered the triad of confidentiality, integrity, and availability.

So, let’s revisit that thesis and how we should view those events through a perspective of risk and engineering.

Eventually Encrypted

For well over a decade, at least two major hurdles blocked pervasive HTTPS. The first was convincing sites to deploy HTTPS in the first place and take on the cost of purchasing certificates. The second was getting HTTPS deployments to use strong configurations that enforced TLS for all connections and only used recommended ciphers.

Setting aside the distinctions between security and compliance, PCI was a crucial driver for adopting strong HTTPS. Having a requirement for transport encryption, backed by financial consequences for failure, has been more successful than asking nicely, raising awareness at security conferences, or shaming. I suspect the rate of HTTPS adoption has been far faster for in-scope PCI sites than others.

The SSL Labs project might also be a factor, but it straddles that line of encouragement through observability and shaming. It distilled a comprehensive analysis of a site’s TLS configuration into a simple letter score. The publically-visible results could be used as a shaming tactic, but that’s a weaker strategy for motivating positive change. Plus, doing so doesn’t address any of the HTTPS hurdles, whether convincing sites to shoulder the cost of obtaining certs or dealing with the overhead of managing them.

Still, SSL Labs provides an easy way for organizations to consistently monitor and evaluate their sites. This is a step towards providing help for migration to HTTPS-only sites. App owners still bear the burden of fixing errors and misconfigurations, but this tool made it easier to measure and track their progress towards strong TLS.

Effectively Encrypted

Where SSL Labs inspires behavioral change via metrics, the Let’s Encrypt project empowers behavioral change by addressing fundamental challenges faced by app owners.

Let’s Encrypt eases the resource burden of managing HTTPS endpoints. It removes the initial cost of certs (they’re free!) and reduces the ongoing maintenance cost of deploying, rotating, and handling certs by supporting automation with the ACME protocol. Even so, solving the TLS cert problem is orthogonal to solving the TLS configuration problem. A valid Let’s Encrypt cert might still be deployed to an HTTPS service that gets a bad grade from SSL Labs.

A cert signed with SHA-1, for example, will lower its SSL Labs grade. SHA-1 has been known weak for years and discouraged from use, specifically for digital signatures. Having certs that are both free and easy to rotate (i.e. easy to obtain and deploy new ones) makes it easier for sites to migrate off deprecated versions. The ability to react quickly to change, whether security-related or not, is a sign of a mature organization. Automation as made possible via Let’s Encrypt is a great way to improve that ability.


Facebook explained their trade-offs along the way to hardening their TLS configuration and deprecating SHA-1. It was an engineering-driven security decision that evaluated solutions and chose among conflicting optimizations – all informed by measures of risk. Engineering is the key word in this paragraph; it’s how systems get built.

Writing down a simple requirement and prototyping something on a single system with a few dozen users is far removed from delivering a service to hundreds of millions of people. WhatsApp’s crypto design fell into a similar discussion of risk-based engineering1. This excellent article on messaging app security and privacy is another example of evaluating risk through threat models.

Exceptional Events

Companies like Cloudflare take a step beyond SSL Labs and Let’s Encrypt by offering a service to handle both certs and configuration for sites. They pioneered techniques like Keyless SSL in response to their distinctive threat model of handling private keys for multiple entities.

If you look at the Cloudbleed report and immediately think a service like that should be ditched, it’s important to question the reasoning behind such a risk assessment. Rather than make organizations suffer through the burden of building and maintaining HTTPS, they can have a service the establishes a strong default. Adoption of HTTPS is slow enough, and fraught with error, that services like this make sense for many site owners.

Compare this with Heartbleed. It also affected TLS sites, could be more targeted, and exposed private keys (among other sensitive data). The cleanup was long, laborious, and haphazard. Cloudbleed had significant potential exposure, although its discovery and remediation likely led to a lower realized risk than Heartbleed.

If you’re saying move away from services like that, what in practice are you saying to move towards? Self-hosted systems in a rack in an electrical closet? Systems that will degrade over time and, most likely, never be upgraded to TLS 1.3? That seems ill-advised.


Does that S3 outage raise concern for cloud-based systems? Not to a great degree. Or, at least, not in a new way. If your site was negatively impacted by the downtime, a good use of that time might have been exploring ways to architect fail-over systems or revisit failure modes and service degradation decisions. Sometimes it’s fine to explicitly accept certain failure modes. That’s what engineering and business do against constraints of resource and budget.

Coherently Considered

So, let’s leave a few exercises for the reader, a few open-ended questions on threat modeling and engineering.

Flash has been long rebuked for its security weaknesses. As with SHA-1, the infosec community voiced this warning for years. There have even been one or two (ok, lots more than two) demonstrated exploits against it. It persists. It’s embedded in Chrome2, which you can interpret as a paternalistic effort to sandbox it or, more cynically, an effort to ensure YouTube videos and ad revenue aren’t impacted by an exodus from the plugin.

Browsers have had impactful vulns, many of which carry significant risk and impact as measured by the annual $50K+ rewards from Pwn2Own competitions. The minuscule number of browser vendors carries risk beyond just vulns, affecting influence on standards and protections for privacy. Yet more browsers doesn’t necessarily equate to better security models within browsers.

Approaching these kinds of flaws with ideas around resilience, isolation, authn/authz models, or feedback loops are just a few traits of a builder. They can be traits for a breaker as well, in creating attacks against those designs.

Approaching these by explaining design flaws and identifying implementation errors are just a few traits of a breaker. They can be traits for a builder as well, in designing controls and barriers to disrupt attacks.

Approaching these by dismissing complexity, designing systems no one would (or could) use, or highlighting irrelevant flaws is often just blather. Infosec has its share of vacuous and overly-ambiguous phrases like military-grade encryption, perfectly secure, artificial intelligence (yeah, I know, blah blah blah Skynet), use-Tor-use-Signal, and more.

There’s a place for mockery and snark. This isn’t concern trolling, which is preoccupied with how things are said. This is about understanding the underlying foundation of what is being said about designs – the risk calculations, the threat models, the constraints.

Constructive Closing


I believe in supporting people to self-identity along the spectrum of builder and breaker rather than pin them to narrow roles – a principle applicable to many more important subjects as well. This is about the intellectual reward of tackling challenges faced by builders and breakers alike, and discarding the blather of uninformed opinions and empty solutions.

I’ll close with this observation from Carl Sagan in The Demon-Haunted World:

It is far better to grasp the universe as it really is than to persist in delusion, however satisfying and reassuring.

Our appsec universe consists of systems and data and users, each in different orbits.

Security should contribute to the gravity that binds them together, not the black hole that tears them apart. Engineering works within the universe as it really is. Shed the delusion that one appsec solution in a vacuum is always universal.

  1. Whatsapp provides great documentation on their designs for end-to-end encryption. 

  2. In 2017 Chrome announced they’d remove Flash by the end of 2020.