9 Rules of Engagement for Penetration Testing

When planning a penetration test, establishing clear Rules of Engagement (RoE) is essential to ensure the test is conducted effectively, ethically, and within the agreed-upon scope. The RoE sets the guidelines for how the penetration testing will be carried out, detailing the procedures, constraints, and expectations that both the testers and the target organization must adhere to.

This ensures that both parties have a mutual understanding of how the test will unfold, helping to prevent misunderstandings, legal issues, and operational disruptions.

Here are the key elements that must be included in the Rules of Engagement:

Timeline and Scheduling
Scope of the Test
Data Handling and Compliance
Expected Defensive Behaviors
Resource Commitments
Legal and Regulatory Considerations
Communication Protocols
Escalation Paths
Authorized Points of Contact

1. Timeline and Scheduling

The timeline for the penetration test is crucial and must be determined in advance. This includes setting specific start and end dates for the engagement, as well as defining the hours during which the testing can be conducted.

In many cases, testing is scheduled during off-peak or noncritical times to minimize the risk of disrupting business operations. For example, testing might occur during nights, weekends, or holidays when system usage is lower.

Alternatively, testing during normal business hours can help simulate real-world attack scenarios and assess the organization’s ability to detect and respond to attacks while operations are running normally.

The overall length of the test should be set to ensure the penetration testers have enough time to carry out a comprehensive assessment while also fitting into the organization’s operational schedule.

2. Scope of the Test

Defining the scope of the penetration test is essential to ensure that all involved parties are aligned on what is included and excluded from the test. Scope definitions prevent unexpected service disruptions and help to focus the testers on areas that need evaluation.

Specify which locations, systems, applications, networks, and devices are included in the test. This ensures that the testers are clear on what they are expected to assess.

It is also important to define any areas that are off-limits to avoid disruption to critical systems or unauthorized access to sensitive environments.

If the target organization uses third-party services such as cloud providers, ISPs, or outsourced security monitoring services, those parties must be informed and considered. Testing their systems could inadvertently cause service outages or breaches, which need to be avoided.

3. Data Handling and Compliance

Handling sensitive data gathered during the penetration test must be done with care, especially when the assessment involves regulated or sensitive environments, such as healthcare or financial sectors.

If the test involves environments with protected health information (PHI), financial data, or other regulated information, the testers must ensure compliance with relevant laws, such as HIPAA or GDPR. This means testers should avoid accessing or exposing sensitive information unless specifically authorized.

Data handling protocols should be clearly defined, including encrypting test results and any sensitive information gathered during the test. Testers may also be required to sign non-disclosure agreements (NDAs).

After the engagement is complete, there should be guidelines on how the test data will be handled and securely disposed of.

4. Expected Defensive Behaviors

Understanding how the target organization will respond to the penetration test is critical. Some organizations have automated defenses that may affect the test’s progress.

Organizations may deploy active defenses such as shunning (ignoring certain network traffic), blacklisting IP addresses, or rate-limiting requests. While these defenses can stop certain attacks, they may also hinder the penetration testers from fully assessing the security of the infrastructure.

In some cases, the goal of the test is to evaluate the organization’s ability to detect and block attacks. In such cases, defensive measures should be left intact. However, if the goal is a complete test of the system’s vulnerabilities, bypassing or disabling certain defenses might be required to allow for full assessment.

5. Resource Commitments

For a successful penetration test, both the penetration testers and the target organization need to allocate the necessary resources.

In white box or gray box scenarios, system administrators, developers, and network engineers may need to be available to answer questions or provide access. Their expertise may be required to navigate complex systems or test particular configurations.

The target organization must ensure that appropriate personnel are informed of the test and are available to address any issues that arise during the engagement.

6. Legal and Regulatory Considerations

Penetration testing can raise various legal and regulatory concerns, especially if it involves third parties or sensitive systems.

Ensure the test complies with all relevant regulations, such as PCI-DSS for payment card systems or HIPAA for healthcare environments.

The RoE must specify that the organization has the legal authority to allow the test, and that third-party vendors or services included in the test are aware of and agree to the testing activities.

7. Communication Protocols

Clear communication channels are vital throughout the testing process to ensure transparency and timely responses to any issues.

Determine whether the testers will provide daily or weekly updates or if communication will be limited to milestone achievements. Some organizations prefer constant updates, while others opt for a final report.

The RoE should specify whom to contact in case of critical events such as evidence of an active compromise, a breach of the RoE, or the discovery of critical vulnerabilities that require immediate attention.

8. Escalation Paths

In case of an emergency, such as detecting an active threat or a severe vulnerability, an escalation plan is essential to ensure swift responses.

The RoE should include a list of contacts for different scenarios, such as a critical vulnerability being found or if testers accidentally cause a service outage. There should be an agreed-upon plan for notifying key stakeholders immediately.

If the penetration test uncovers signs of an ongoing breach, the organization’s incident response team should be alerted immediately to address the threat in real-time.

9. Authorized Points of Contact

To prevent confusion and avoid delays, the RoE must specify who has the authority to interact with the penetration testers and request updates or changes to the engagement.

Define which personnel from the target organization can request updates or give instructions to the testers. For instance, it might be specified that only members of the security team or IT leadership can communicate with the penetration testers.

This prevents situations where unauthorized personnel, such as a CFO or department manager, might try to engage the testers without proper context or authority.

Conclusion

Establishing well-defined Rules of Engagement (RoE) is crucial for the success of any penetration test. The RoE serves as the blueprint for how the test will be conducted, covering all aspects from scope and timeline to legal considerations and communication protocols.

By outlining these rules, both the penetration testers and the target organization can ensure that the test is conducted safely, effectively, and in compliance with legal and operational requirements.

You may also like: