Test Your Cybersecurity Defenses with Penetration Testing and Red Team Exercises

Today’s cyberattacks are unlike those from twenty, thirty years ago. When ransomware attacks were first introduced, the primary driver for their use was money. Cybercriminals didn’t care if the money came from businesses–at best, they stood to gain a few hundred dollars from each victim. Today, it’s about a lot more than just money.

In recent years, although cybercriminals have been driven by greed, they’ve also been driven by inflicting chaos on society by shutting down critical infrastructure. What’s more is that cybercriminals have adapted their internal operations to achieve their goals.

Unfortunately, organizations aren’t always able to keep up. A new ransomware study, conducted by the CyberRisk Alliance, found that 37% of respondents said they lack an adequate cybersecurity budget and 31% can’t prevent a ransomware attack because cybercriminals are too well-funded and sophisticated.

The challenge is that cybercriminals will do everything they can to gain access into your environment so, how do you know your current cybersecurity defenses are strong enough? You need to test your defenses continuously.

In this blog, we’ll highlight the difference between penetration testing and red team exercises, and when you should engage both services.

What is penetration testing?

Pen testing, or penetration testing, allows your cybersecurity team to test your current defenses against simulated attacks and identify weaknesses in your external or internal security posture. Pen testers use the latest tactics, techniques, and procedures (TTPs) that adversaries are utilizing to infiltrate and exploit systems and gain access to data.

Therefore, pen testing is an integral aspect of managing, and reducing, your cyber risk since the goal is to identify systematic weaknesses present in your environment and discover areas of greatest risk and remediation. Pen testing also enables you to satisfy compliance needs and validate the existing internal and/or external cybersecurity controls.

Without putting your team through routine pen testing exercises, you limit your ability to determine how your cybersecurity teams need to adapt to the ever-evolving adversarial TTPs.

What is a red team exercise?

A red team exercise is a simulation of an advanced threat actor to test your organization's prevention, detection, and response capabilities and is a more in-depth than a penetration test. It combines various techniques to evade detection and prevention capabilities, including OSINT, phishing, wireless and covert physical and network attack tactics, techniques, and procedures (TTPs).

After the engagement, you get an assessment in your team’s capability of successfully preventing, detecting, and responding to a real-world cyberattack and identify areas of greatest risk and remediation recommendations.

Red team engagements are especially necessary considering many organizations don’t have the capabilities needed to prevent an adversary from successfully attacking their organization. In a 2021 pen testing survey conducted by eSentire, we found that only 32% of organizations have the detection and response capabilities they need to deter a real-world adversary.

Penetration testing vs. red team exercise: which one is right for me?

Often, organizations think that they can choose between a pen testing engagement and a red team exercise because both will uncover the same results. However, this isn’t true since the objective of these services is completely different.

The objective of a pen test is to identify the easiest entry points into your environment and provide your team with all the gaps found, ranked from most critical to the least critical. In other words, a pen test uncovers any vulnerabilities and weaknesses found on the assets you’re testing, such as web applications, mobile applications, or wireless access points. Plus, your team doesn’t try to defend against the pen tester’s actions during the testing process.

On the other hand, a red team exercise is similar to a head-to-head battle, during which the red team tries to break into your systems by mimicking advanced tactics and techniques and your in-house cybersecurity team tries to actively keep them out. The key differentiator is that your team isn’t aware that they’re defending against the attacks as part of a red team exercise–they believe they are defending against a real threat actor.

In addition, a red team engagement also takes longer than a pen testing engagement because the red team will validate physical security controls (e.g., gaining access into a secure office building) in addition to virtual security controls.

Ideally, you should be conducting a pen test and a red team exercise on a regular basis. We recommend performing each engagement annually, at a minimum.

Given how cybercriminals are evolving their operations and strategies, and how accessible it is for new threat actors to target companies using the ransomware-as-a-service model, your cybersecurity team must test your defenses to ensure you can thwart a cyberattack when the time comes.

Learn how eSentire’s Managed Risk Programs can help your organization test your cybersecurity defenses through by booking a meeting with us today.