In the realm of cybersecurity pen-testing, the Rules of Engagement (ROE) are pivotal for structured, ethical hacking and vulnerability assessments. They specify what can and cannot be done during a red team engagement, ensuring that the testing is both controlled and ethical. However, while these rules are essential, they can sometimes foster a false sense of security. Here’s why:

Understanding Rules of Engagement (ROE)

ROE are agreements between the red team and the client that outline the scope, methods, and boundaries of the engagement. They protect both parties, ensuring that the assessment is conducted ethically and legally. Typical elements of ROE include authorized actions, restricted targets, engagement objectives, and compliance with legal requirements.

The Comfort of Boundaries

Having clear boundaries can be reassuring. Organizations might feel confident knowing that their security is being tested within defined limits. However, real-world attackers don’t play by these rules. They exploit vulnerabilities without regard for ethical boundaries or predefined scopes.

ROE are designed to prevent damage and disruption during tests, which means some areas might be off-limits. These restrictions can leave certain vulnerabilities untested. For example, if specific systems or data are excluded from the engagement, it creates blind spots that attackers could exploit. The safety net provided by ROE can sometimes mask these blind spots, giving a false impression of overall security.

Red team engagements simulate attacks to test defences. However, these simulations are inherently limited by the ROE. An over-reliance on these controlled tests can lead to complacency. Organizations might believe they’re secure because they performed well against simulated attacks, while in reality, they might not be prepared for the full spectrum of real-world threats.

The Need for Continuous Assessment

Cybersecurity is not a one-time activity. The threat landscape is constantly evolving, and so should security measures. While ROE-based engagements are valuable, they should be part of a broader, continuous assessment strategy. Regular vulnerability scans, real-time monitoring, and adaptive defences are crucial to staying ahead of threats.

To mitigate the risks of a false sense of security, it’s essential to balance control with realism. This can be achieved by:

• Periodically expanding the scope of engagements to cover previously excluded areas.

• Conducting surprise assessments with minimal ROE restrictions.

• Integrating red team findings with other security measures for a comprehensive defence strategy.

Considerations for Defining ROE

When defining ROE, it’s crucial to include comprehensive considerations to ensure a realistic and valuable assessment

Inclusions:

• Critical Systems: Include systems that are vital to business operations to identify potential weaknesses.

• Legacy Applications: Despite their sensitivity, including legacy applications can reveal hidden vulnerabilities.

• User Privileges: Assess different user levels, from regular users to administrators, to find privilege escalation risks.

Exclusions:

• Safety and Compliance: Certain systems might be excluded to avoid compliance violations or operational disruptions.

• Sensitive Data: Personally identifiable information (PII) and other sensitive data might be off-limits to prevent data breaches.

• Operational Continuity: Systems critical to day-to-day operations might be excluded to avoid downtime.

Conclusion

Rules of Engagement are vital for structured and ethical security testing. However, they can also create an illusion of safety if not used wisely. By understanding their limitations and integrating them into a broader, continuous security strategy, organizations can ensure they’re truly prepared for the unpredictable nature of real-world cyber threats.

By carefully considering what to include and exclude in ROE, organizations can achieve a balance between thorough testing and operational safety. This holistic approach ensures that the security assessments are realistic, comprehensive, and truly reflective of the organization’s security posture.