Home Did you know ? 3 Challenges of Penetration Testing and How to Solve Them

3 Challenges of Penetration Testing and How to Solve Them

by Mic Johnson

Penetration tests are one of the best ways of testing your network for vulnerabilities. However, many companies struggle to extract maximum value from them due to certain challenges. These challenges occur because a lot of the work that ensures a pentest’s success has to be carried out before the test even begins.

Overcoming these challenges isn’t easy, but thanks to advances in cybersecurity, t’s far from impossible to do so. Here’s how you can address them and extract the most from your penetration tests.

Challenge #1: Scope Creep

The scoping stage of a test is the most critical period. There are many things to test and different ways to test all of them. In the name of covering all bases, you might end up doing a little bit of everything. The result is that your previously focused pentest is now bloated, and no one knows what is being tested anymore.

Organizations think that broad pentests are better than focused ones. Their reasoning is understandable. A broad test, on paper, covers more assets and provides the perception of risk reduction. However, going shallow is never the solution. So what should you do? The answer is to turn to an established security framework.

Security frameworks remove the guesswork from test definitions by providing organizations with a template of attack vectors and security best practices. A shining example of this is the MITRE ATT&CK framework. ATT&CK maps the most relevant threats and attack methods currently out there and gives you clear insight into your system’s vulnerabilities.

Before frameworks like MITRE ATT&CK were established, threat modeling was a mixture of using open-source attack tools and manually simulated threats. Mapping your pentest to the MITRE ATT&CK framework isn’t a holy grail. However, it’s a good way to prevent scope creep and get started on the right foot.

Challenge #2: Time and Resource Constraints

Once organizations move past the scoping stage, they discover that they lack the resources or time to conduct a thorough pentest. It’s no secret that cybersecurity is a scarce skill, and it’s tough to find professionals who can stay up to speed with ever-evolving threats.

Limiting scope creep is the first step to ensuring your limited pentesting resources aren’t wasting time on mundane tasks. The next step is to automate as much of the process as possible. These days you can use tools that will help you carry out automated penetration testing.

An automated tool will help you model the latest threats against your system and simulate attack techniques daily. Your pentesting team can focus on evaluating the results of these attacks and customizing attack paths into your system.

This method is opposed to the manual version where your pentesting team has to carry out simulated attacks repeatedly over a period of time and then review results. Valuable time is lost as a result, and just as you begin to make sense of your results, there’s a good chance that your threats have evolved beyond the versions you tested.

Another benefit an automated tool provides is that it can recommend mitigation scenarios based on security best practices. Your pentesting team can remove guesswork from the process and immediately dive into mitigation scenarios mapped to security best practices.

As a result, your cybersecurity protocols move from a one-time approach to a continuous or always-on model. Your network’s security posture becomes more robust and evolves with the threats it faces. Most cybersecurity threats these days use AI to learn the networks they’re attacking.

A static posture leaves you vulnerable to a second or third attack where the algorithm has learned your network and has discovered flaws in it. The only way to combat this threat is to conduct automated security effectiveness testing and continuously optimize your infrastructure.

Challenge #3: Dealing With APTs

APTs or Advanced Persistent Threats are the bane of a pentesting team. Many automated security testing tools fail to deal with APTs because they cannot model all attack vectors that are currently relevant. As a result, your organization risks adopting a static security model despite automating threat modeling.

By using a tool mapped to a framework that is tied to security best practices, you can rest assured that the attack vectors you’re simulating are up to date and that you’re testing the full attack kill-chain.

A robust solution will also allow you to design your own APT from a set of standard templates mapped to the latest APT kill chains. You can design worst-case scenarios and test the limits of your network’s security in a controlled environment. Choose an automated solution that updates its library every day with the latest threats you face and with the latest recommendations from a proven framework.

Dynamic and Secure

A dynamic cybersecurity model is the way forward if you want to deal with ever-evolving threats. The MITRE ATT&CK framework offers a great roadmap for your organization, but you need to back it up with intelligent automation. Neglect this, and your pentesting team will be stretched thin and unable to focus on the tasks that truly make a difference to your security posture.

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