We have been fans of testing the security of infrastructure and applications as long as we can remember doing research. We have always known attackers are testing your environment all the time, so if you aren’t also self-assessing, inevitably you will be surprised by a successful attack. And like most security folks, we are no fans of surprises.

Security testing and assessment has gone through a number of iterations. It started with simple vulnerability scanning. You could scan a device to understand its security posture, which patches were installed, and what remained vulnerable on the device. Vulnerability scanning remains a function at most organizations, driven mostly by a compliance requirement.

As useful as it was to understand which devices and applications were vulnerable, a simple scan provides limited information. A vulnerability scanner cannot recognize that a vulnerable device is not exploitable due to other controls. So penetration testing emerged as a discipline to go beyond simple context-less vulnerability scanning, with humans trying to steal data.

Pen tests are useful because they provide a sense of what is really at risk. But a penetration test is resource-intensive and expensive, especially if you use an external testing firm. To address that, we got automated pen testing tools, which use actual exploits in a semi-automatic fashion to simulate an attacker.

Regardless of whether you use carbon-based (human) or silicon-based (computer) penetration testing, the results describe your environment at a single point in time. As soon as you blink, your environment will have changed, and your findings may no longer be valid.

With the easy availability of penetration testing tools (notably the open source Metasploit), defending against a pen testing tool has emerged as the low bar of security. Our friend Josh Corman coined HDMoore’s Law, after the leader of the Metasploit project. Basically, if you cannot stop a primitive attacker using Metasploit (or another pen testing tool), you aren’t very good at security.

The low bar isn’t high enough

As we lead enterprises through developing security programs, we typically start with adversary analysis. It is important to understand what kinds of attackers will be targeting your organization and what they will be looking for. If you think your main threat is a 400-pound hacker in their parents’ basement, defending against an open source pen testing tool is probably sufficient.

But do any of you honestly believe an unsophisticated attacker wielding a free penetration testing tool is all you have to worry about? Of course not. The key thing to understand about adversaries is simple: They don’t play by your rules. They will attack when you don’t expect it. They will take advantage of new attacks and exploits to evade detection. They will use tactics that look like a different adversary to raise a false flag.

The adversary will do whatever it takes to achieve their mission. They can usually be patient, and will wait for you to screw something up. So the low bar of security represented by a pen testing tool is not good enough.

Dynamic IT

The increasing sophistication of adversaries is not your only challenge assessing your environment and understanding risk. Technology infrastructure seems to be undergoing the most significant set of changes we have ever seen, and this is dramatically complicating your ability to assess your environment.

First, you have no idea where your data actually resides. Between SaaS applications, cloud storage services, and integrated business partner networks, the boundaries of traditional technology infrastructure have been extended unrecognizably, and you cannot assume your information is on a network you control. And if you don’t control the network it becomes much harder to test.

The next major change underway is mobility. Between an increasingly disconnected workforce and an explosion of smart devices accessing critical information, you can no longer assume your employees will access applications and data from your networks. Realizing that authorized users needing legitimate access to data can be anywhere in the world, at any time, complicates assessment strategies as well.

Finally, the push to public cloud-based infrastructure makes it unclear where your compute and storage are, as well. Many of the enterprises we work with are building cloud-native technology stacks using dozens of services across cloud providers. You don’t necessarily know where you will be attacked, either.

To recap, you no longer know where your data is, where it will be accessed from, or where your computation will happen. And you are chartered to protect information in this dynamic IT environment, which means you need to assess the security of your environment as often as practical. Do you start to see the challenge of security assessment today, and how much more complicated it will be tomorrow?

We Need Dynamic Security Assessment

As discussed above, a penetration test represents a point in time snapshot of your environment, and is obsolete when complete, because the environment continues to change. The only way to keep pace with our dynamic IT environment is dynamic security assessment. The rest of this series will lay out what we mean by this, and how to implement it within your environment.

As a little prelude to what you’ll learn, a dynamic security assessment tool includes:

  • A highly sophisticated simulation engine, which can imitate typical attack patterns from sophisticated adversaries without putting production infrastructure in danger.
  • An understanding of the network topology, to model possible lateral movement and isolate targeted information and assets.
  • A security research team to leverage both proprietary and public threat intelligence, and to model the latest and greatest attacks to avoid unpleasant surprises.
  • An effective security analytics function to figure out not just what is exploitable, but also how different workarounds and fixes will impact infrastructure security.

We would like to thank SafeBreach as the initial potential licensee of this content. As you may remember, we research using our Totally Transparent Research methodology, which requires foresight on the part of our licensees. It enables us to post our papers in our Research Library without paywalls, registration, or any other blockage to you reading (and hopefully enjoying) our research.

We will start describing Dynamic Security Assessment in our next post.