Introduction

Proper documentation is crucial for cybersecurity assessments, but it can also be a dry and technical topic. In this blog post, we’ll explore how documentation can make or break a red team engagement, and how to make it more engaging for both the team and stakeholders.

Why Documentation Matters

Ensures Consistency: Nobody likes surprises when it comes to cybersecurity, and proper documentation can help ensure consistency across different systems and processes. By having a clear record of the assessment process, the team can avoid errors or inconsistencies that could compromise the engagement.

Provides a Reference Point: Documentation serves as a reference point for the assessment process, allowing the team to review their progress and identify areas for improvement. It also provides a reference point for stakeholders to understand the assessment process and results, which can be especially important if they’re not familiar with cybersecurity.

Facilitates Communication: Documentation provides a common language and understanding among team members, stakeholders, and vendors. It facilitates communication and collaboration among team members and helps ensure that everyone is working towards the same goals. Plus, it can make the process more interesting and engaging for everyone involved.

Enhances Transparency: Transparency is key when it comes to cybersecurity assessments, and proper documentation can help build trust and confidence in the team’s work. By providing stakeholders with visibility into the assessment process and results, the team can show that they’re accountable and trustworthy.

Enables Repeatability: Repeatability is important for organizations that want to track their progress in addressing security risks and vulnerabilities. Proper documentation enables the assessment to be repeated over time, so organizations can ensure that security controls are working effectively.

Facilitates Compliance: Proper documentation is essential for compliance with regulatory requirements and industry standards. It provides a record of the assessment process, results, and remediation efforts, which can be used to demonstrate compliance with relevant regulations and standards.

Engagement Planning

To make documentation more engaging, it’s important to approach it as part of the larger engagement planning process. Here are some tips for doing so:

Scope, Objectives, & Operation Documentation: Before the engagement even begins, it’s important for the client and red team to agree on the objectives, scope, and rules of engagement. By documenting these details, the team can ensure that they’re on the same page and avoid misunderstandings or conflicts later on.

Rules of Engagement (ROE): Rules of engagement are essential for ensuring that the engagement is conducted in a professional and responsible way. By documenting the ROE, the team can ensure that everyone is clear on what is and isn’t allowed during the engagement.

Campaign Planning: The red team should use the information gathered from the client objectives and ROE to create a range of strategies, plans, and activities that are designed to attain their objectives. These plans and documents can be made more engaging by including visuals, real-world examples, and scenarios.

Checklists: Checklists are a simple but effective way to make documentation more engaging. By breaking down complex processes into a series of manageable steps, checklists can make the engagement process more approachable and less overwhelming.

Remediation Planning

Once the engagement is complete, the team will need to develop a remediation plan to address any vulnerabilities or weaknesses that were identified. Here are some tips for making remediation planning more engaging:

• Prioritization of Issues: The team can make the remediation process more manageable and interesting by organizing issues and concentrating on the most important vulnerabilities. They gain a better understanding of which vulnerabilities are most important and call for rapid response. To make sure that the most important vulnerabilities are fixed first, this might help them prioritize remediation activities and allocate resources accordingly.
• Actionable Steps: The remediation plan should include clear and concise actionable steps. The team can make the process more approachable and engaging by breaking complex issues down into simple steps. Incorporating actionable steps into remediation planning can be extremely beneficial to stakeholders. Stakeholders can better understand the remediation process and feel more involved if complex issues are broken down into simple, actionable steps.
• Timeline: Include a timeline for each event, including start and end dates as well as any intermediate milestones. Stakeholders can track the progress of remediation efforts and ensure that they are on track to meet the set goals and objectives by outlining a timeline with specific start and end dates. Furthermore, having a clear timeline can assist stakeholders in better planning their own activities and allocating resources, resulting in a more efficient use of time and money.
• Assigned Responsibilities: Determine who will be in charge of each action item, including any assistance required from other departments or stakeholders. By including assigned responsibilities, stakeholders can clearly see who is responsible for each action item and hold them accountable for their progress. This can help to increase transparency and trust in the remediation process, which is essential for effective cybersecurity risk management.
• Resource Requirements: Determine what resources, such as personnel, tools, or funding, will be needed to carry out the remediation plan. It assists them in understanding the level of investment necessary to address the identified vulnerabilities or weaknesses. This data can be used to prioritize remediation efforts and allocate resources. Furthermore, it can assist stakeholders in planning and budgeting for the necessary resources, whether personnel, tools, or funding.
• Risk Management: Incorporating risk management into remediation planning can benefit stakeholders in a variety of ways. For starters, it aids in the identification and mitigation of potential risks associated with remediation efforts, which can help prevent future security breaches and other incidents. Stakeholders can be confident that their organization is proactively addressing cybersecurity risks by developing risk management strategies. Furthermore, by demonstrating the organization’s commitment to transparency, accountability, and responsible security practices, risk management can help to build trust and confidence among stakeholders. Finally, organizations can help to reduce the impact of future security incidents by considering potential risks and developing risk management strategies, saving time, money, and resources in the long run.

Conclusion

Proper documentation is essential for successful red team engagements. It not only helps ensure consistency and transparency but also provides a reference point for assessing progress and identifying areas for improvement. By making documentation part of the engagement planning process and using engaging techniques such as visuals and checklists, red teams can ensure that all stakeholders are on the same page and engaged in the process. By following the tips outlined in this post, red teams can create a more effective remediation plan and ultimately, help organizations better protect themselves against cyber threats.

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My name is Quinyon Nave, aka Digital Quinn, and I am an Active Duty Soldier and the Founder of Nave Security. I want to be a cybersecurity pioneer and teach others about data and information security. My other professional ambition is to research the brain and create new forms of neuro-biomedical technology. I am an outspoken proponent of self-love and self-care, and I am on a mission to spread positivity throughout the world.