Executing Red Team Engagement Planning

Overview

Red team engagement planning is the foundational phase that defines scope, objectives, rules of engagement (ROE), threat model selection, and operational timelines before any offensive testing begins. A well-structured engagement plan ensures the red team simulates realistic adversary behavior while maintaining safety guardrails that prevent unintended business disruption.

Objectives

• Define clear engagement scope including in-scope and out-of-scope assets, networks, and personnel
• Establish Rules of Engagement (ROE) with emergency stop procedures, communication channels, and legal boundaries
• Select appropriate threat profiles from the MITRE ATT&CK framework aligned to the organization's threat landscape
• Create a detailed attack plan mapping adversary TTPs to engagement objectives
• Develop deconfliction procedures with the organization's SOC/blue team
• Produce a comprehensive engagement brief for stakeholder approval

Core Concepts

Engagement Types

Type	Description	Scope
Full Scope	Complete adversary simulation with physical, social, and cyber vectors	Entire organization
Assumed Breach	Starts from initial foothold, focuses on post-exploitation	Internal network
Objective-Based	Target specific crown jewels (e.g., domain admin, PII exfiltration)	Defined targets
Purple Team	Collaborative with blue team for detection improvement	Specific controls

Rules of Engagement Components

1. Scope Definition: IP ranges, domains, physical locations, personnel
2. Restrictions: Systems/networks that must not be touched (e.g., production databases, medical devices)
3. Communication Plan: Primary and secondary contact channels, escalation procedures
4. Emergency Procedures: Code word for immediate cessation, incident response coordination
5. Legal Authorization: Signed authorization letters, get-out-of-jail letters for physical tests
6. Data Handling: How sensitive data discovered during testing will be handled and destroyed
7. Timeline: Start/end dates, blackout windows, reporting deadlines

Threat Profile Selection

Map organizational threats using MITRE ATT&CK Navigator to select relevant adversary profiles:

• APT29 (Cozy Bear): Government/defense sector targeting via spearphishing, supply chain
• APT28 (Fancy Bear): Government organizations, credential harvesting, zero-days
• FIN7: Financial sector, POS malware, social engineering
• Lazarus Group: Financial institutions, cryptocurrency exchanges, destructive malware
• Conti/Royal: Ransomware operators, double extortion, RaaS model

Implementation Steps

Phase 1: Pre-Engagement

1. Conduct initial scoping meeting with stakeholders
2. Identify crown jewels and critical business assets
3. Review previous security assessments and audit findings
4. Define success criteria and engagement objectives
5. Draft Rules of Engagement document

Phase 2: Threat Modeling

1. Identify relevant threat actors using MITRE ATT&CK
2. Map threat actor TTPs to organizational attack surface
3. Select primary and secondary attack scenarios
4. Define adversary emulation plan with specific technique IDs
5. Establish detection checkpoints for purple team opportunities

Phase 3: Operational Planning

1. Set up secure communication channels (encrypted email, Signal, etc.)
2. Create operational security (OPSEC) guidelines for the red team
3. Establish infrastructure requirements (C2 servers, redirectors, phishing domains)
4. Develop phased attack timeline with go/no-go decision points
5. Create deconfliction matrix with SOC/IR team

Phase 4: Documentation and Approval

1. Compile engagement plan document
2. Review with legal counsel
3. Obtain executive sponsor signature
4. Brief red team operators on ROE and restrictions
5. Distribute emergency contact cards

Tools and Resources

• MITRE ATT&CK Navigator: Threat actor TTP mapping and visualization
• VECTR: Red team engagement tracking and metrics platform
• Cobalt Strike / Nighthawk: C2 framework planning and infrastructure design
• PlexTrac: Red team reporting and engagement management platform
• SCYTHE: Adversary emulation platform for attack plan creation

Validation Criteria

• [ ] Signed Rules of Engagement document
• [ ] Defined scope with explicit in/out boundaries
• [ ] Selected threat profile with mapped MITRE ATT&CK techniques
• [ ] Emergency stop procedures tested and verified
• [ ] Communication plan distributed to all stakeholders
• [ ] Legal authorization obtained and filed
• [ ] Red team operators briefed and acknowledged ROE

Common Pitfalls

1. Scope Creep: Expanding testing beyond approved boundaries during execution
2. Inadequate Deconfliction: SOC investigating red team activity as real incidents
3. Missing Legal Authorization: Testing without proper signed authorization
4. Unrealistic Threat Models: Simulating threats irrelevant to the organization
5. Poor Communication: Failing to maintain contact with stakeholders during engagement

Related Skills

• performing-open-source-intelligence-gathering
• conducting-adversary-simulation-with-atomic-red-team
• performing-assumed-breach-red-team-exercise
• building-red-team-infrastructure-with-redirectors

Compliance Framework Mapping

This skill supports compliance evidence collection across multiple frameworks:

• SOC 2: CC4.1 (Monitoring & Evaluation), CC7.1 (Monitoring)
• ISO 27001: A.14.2 (Secure Development), A.18.2 (Information Security Reviews)
• NIST 800-53: CA-8 (Penetration Testing), RA-5 (Vulnerability Scanning)
• NIST CSF: ID.RA (Risk Assessment), PR.IP (Information Protection)

Claw GRC Tip: When this skill is executed by a registered agent, compliance evidence is automatically captured and mapped to the relevant controls in your active frameworks.

Deploying This Skill with Claw GRC

Agent Execution

Register this skill with your Claw GRC agent for automated execution:

# Install via CLI
npx claw-grc skills add executing-red-team-engagement-planning

# Or load dynamically via MCP
grc.load_skill("executing-red-team-engagement-planning")

Audit Trail Integration

When executed through Claw GRC, every step of this skill generates tamper-evident audit records:

• SHA-256 chain hashing ensures no step can be modified after execution
• Evidence artifacts (configs, scan results, logs) are automatically attached to relevant controls
• Trust score impact — successful execution increases your agent's trust score

Continuous Compliance

Schedule this skill for recurring execution to maintain continuous compliance posture. Claw GRC monitors for drift and alerts when re-execution is needed.