The Human Edge Beyond Pentesting – Building True Cyber Resilience

The Human Edge Beyond Pentesting – Building True Cyber Resilience

Pentest vs. Red Team: Understanding the Core Difference

Many cybersecurity vendors are rebadging pentesting as attack simulations or red teaming, often at a higher cost. However, there's a clear difference:

• Pentesting (Penetration Testing): The overarching goal of penetration testing is to find vulnerabilities within an environment in order to create a remediation plan. Reporting focuses on documenting as many vulnerabilities as possible in the allotted timeframe. 
• Red Teaming (Attack Simulation): In contrast, red teaming is used to validate the efficacy of the defensive (blue) team. It is not looking for vulnerabilities per se, it is about achieving the objectives while trying to avoid detection. Reporting focuses on finding defensive gaps and assessing the blue team's response capabilities. The ultimate goal is to simulate real-world adversaries and determine if the defensive team has the telemetry to detect them.

The key takeaway is that if the engagement isn't assessing your detection capabilities, it is not a red team.

When Does Red Teaming Truly Add Value?

While valuable, red teaming isn't always the most cost-effective solution, and really it is usually only effective in these three scenarios:

1. When You Have a Regulatory Requirement: Industries with specific regulations, such as BEST, TIBER, FEER, CORIE, and AASE, often mandate regulatory red teams, which have standardized approaches and qualifications.
2. When You Have a Very Mature Organization: Your organization has addressed all other possible security issues and has limited justification for further spending, a Red Team can provide a level of assurance that few other testing strategies can match. However, if you have known, unaddressed issues, red teaming rapidly loses value as the simulated attackers will typically take the easiest route to compromise and report on issues you are already aware of.
3. When You Need a "Burning Platform": Sometimes, demonstrating the potential severity of a worst-case scenario is necessary to secure critical budget increases. Red teaming can effectively highlight how badly wrong things could go, aiding CISOs in getting the needed resources.

However, it's important to note that more cost-effective methods often offer a better return on investment than red teaming outside these specific use cases. Purple teaming offers a more holistic approach to measuring your blue team's capability while also having a much higher knowledge transfer rate. Attack path mapping is far more comprehensive in discovering what attackers can do and what vulnerabilities or misconfigurations can be chained together to achieve compromise.

The Pitfalls of Misaligned Red Teaming

Several factors can hinder the benefits of red teaming outside the identified use cases:

• Resource Intensive: Red teaming is both costly and time-consuming.
• Potentially Divisive: It can sometimes lead to conflict between teams or erode trust within an organization.
• Weak Follow-Up: Lessons learned from red team exercises are often not translated into actionable steps, or worse completely ignored.
• Limited Scope: It may fail to explore cascading impacts and real-world disruptions.
• Insufficient Business Focus: Without an understanding of broader business consequences, the exercise's value can be limited.
• Increased Risk: Poorly executed red teaming can introduce wasted effort or unnecessary investigations.
• Often Undetected: A significant number of red team operations do not trigger alerts or go unnoticed by defensive teams. This last point highlights the importance of understanding why an attack wasn't detected, by asking: Was an alert generated? Was it marked as a false positive? Was a process followed? Was the process correct?

Enhancing Cyber Resilience: A Holistic Approach

Cyber resilience is not just about products or individual tools; it's about the application of skilled and motivated people, understanding and utilizing technology, and implementing reliable and repeatable processes and detections. The focus should be on building a robust, layered defense that understands, anticipates, and mitigates all phases of the attack chain, recognizing that the perimeter is no longer the sole objective for attackers.

To truly improve cyber resilience, organizations need to focus on three key areas:

1. Security Posture: Continuously assess and strengthen your foundational security.
2. Detection Capability: Improve your ability to identify and triage malicious activity.
3. Response Capability: Enhance your team's efficiency and effectiveness in reacting to and recovering from incidents.

This involves exposing defenders to real-world Tactics, Techniques, and Procedures (TTPs) relevant to their environment. Furthermore, understanding the capabilities and blind spots of both your security team and defensive tooling is crucial for applying and testing effective mitigations and proving resiliency.

Practical Approaches to Building Resilience

To achieve true benefit from simulations, organizations must prepare individuals and teams before and after the simulation. This involves a cycle of "Prepare & Protect" and "Detect & Respond".

Effective training and exercises are vital for different audiences:

• Individual Preparation: Hands-on labs can provide technical training for various roles, including defensive cybersecurity professionals, penetration testers, developers, application security experts, and cloud & infrastructure security personnel.
• Technical Team Exercises (Team Sim): These focus on the technical aspects of cyber attack and response using pre-configured cyber range scenarios. Participants investigate or perform simulated attacks using real cybersecurity tools and techniques in a safe environment/sandbox. 
• Executive & Business Exercises (Crisis Sim): Moving beyond traditional tabletop exercises, Crisis Sim puts teams into dynamic crisis simulations with real crises, dynamic storylines, and contextual media. This helps measure and benchmark responses to inform crisis strategies and build muscle memory through regular exercising.

By understanding the distinct roles of pentesting and red teaming, strategically applying attack simulations, and investing in comprehensive training across all levels of the organization, businesses can genuinely enhance their cyber resilience and gain the human edge over cyber attacks.