Red Team Engagement

Red Team Engagement — Authorized Adversary Emulation

This skill is for planning and executing an authorized red-team engagement against systems and an organization that has explicitly contracted for it. It is distinct from a penetration test (technique-focused; see web-pentest) and from threat hunting (defensive; see threat-hunting). A red-team engagement is multi-week, objective-based, often assumed-breach, and explicitly tries to test the blue team's detect-and-respond capability — not just to find vulnerabilities.

This is the most dual-use skill in this catalog. The skill refuses to help conduct unauthorized adversary simulation, regardless of how the request is framed. The authorization check below is enforced strictly.

Authorization Check — required before any planning or execution

Before working with this skill at all, confirm:

1. Written authorization for this specific engagement, against this specific target, signed by an executive with authority to grant it. The "get-out-of-jail" letter — a physical / digital document the team can produce if challenged 2. Defined scope — what systems, what time windows, what techniques are in / out of scope 3. Identified target organization owns the target systems — not a third party (vendor, customer, sub-tenant) whose authorization has not been obtained 4. Defined success criteria — what does this engagement need to demonstrate or test 5. Identified deconfliction contact — a single internal person who can pause / abort the engagement and answer "is this you?" when the blue team finds activity 6. Legal review on file — engagement contract or internal authorization reviewed by counsel, including for any controlled-data exposure 7. Communication plan for unintended impact — what happens if production is affected, how is it reported, how fast

If any of the above is missing or unclear, stop. Ask the user to confirm. Do not proceed with planning, technique selection, or any execution work.

If the user describes a target that does not appear to belong to them or to a contracted client, refuse — this is not a misunderstanding to be cleared up by adding "for educational purposes" or "in a CTF." The skill refuses to help simulate an attack on systems whose authorization is not present.

What red-team engagements are for (and what they are not for)

Red-team engagements exist to test the security program's response capability — not just to find vulnerabilities. A good red-team engagement answers questions like:

• If an attacker gets initial access, how long until the blue team notices?
• When the blue team notices, how fast and how completely do they contain it?
• Are the documented incident-response procedures actually used?
• Do detections that exist in theory actually fire in practice?
• Can a determined adversary escalate to the named crown-jewel objective?

Red-team engagements are not for:

• Vulnerability discovery — pentests do that with much less overhead
• Compliance check-box — engagements are designed to teach, not to pass
• Performance reviews — using a red-team engagement to evaluate individual blue-team employees creates incentive problems that distort everyone's behavior

If the goal is "find vulnerabilities," use web-pentest or the relevant audit skill. If the goal is "test whether our detection and response actually works," this is the right skill.

Engagement model — three flavors

Assumed-breach is the most common modern engagement model — the value-per-week is highest because almost every real breach starts with the perimeter already past. Pure external red teams are valuable but expensive in calendar time.

Engagement lifecycle

Phase 0 — Pre-engagement (4-8 weeks before kickoff)

Scoping with the client / sponsor:

• Objectives — what crown-jewel access or capability does the engagement need to demonstrate? "Access customer data at rest" is concrete; "find what you can" is not
• In-scope assets — specific environments, specific subnets, specific applications. List by name, not by description
• Out-of-scope assets — explicitly named. Third-party SaaS, customer data of named accounts, specific production systems, executive personal accounts, regulated data the contract does not cover
• Time window — engagement window with start and end dates. Tighter windows force focus; longer windows allow assumed-breach scenarios to play out
• Techniques out of scope — what the team will NOT do regardless of value. Common: destructive techniques, modification of customer data, mass-exfiltration of real customer data, social engineering of named executives, physical access without separate authorization
• Trusted-agent ("white cell") identification — minimum number of internal people who know the engagement is happening. Typically 2-4: executive sponsor, security leadership, deconfliction contact, legal
• Reporting cadence — daily standup, weekly checkpoint, end-of-engagement debrief
• Communication channels — secure out-of-band (Signal, encrypted email, dedicated bridge) so that the engagement does not leak to the blue team during execution

Documentation deliverables before kickoff:

• Signed Rules of Engagement (RoE) — the contract between the red team and the sponsor
• Get-out-of-jail letter (physical and digital), signed by an authorized executive
• Engagement plan with objectives, scope, techniques planned (per-objective; not a complete attack list)
• Communication / escalation matrix

Phase 1 — Reconnaissance and intelligence (per the engagement type)

For external engagements, leverage recon and osint-recon. For assumed-breach engagements, this phase is internal recon from the granted starting position.

The output is a target map — the systems, accounts, and pivots the team will work through to reach the objective.

Phase 2 — Execution

Following an ATT&CK emulation plan tailored to the engagement.

Emulation plans are published playbooks of how specific threat actors operate. Use them as starting points, not scripts:

• MITRE ATT&CK Emulation Plans — open-source, threat-actor-specific (APT29, FIN6, FIN7, menuPass, OilRig, Carbanak, Sandworm, etc.). Available at attack.mitre.org/resources/adversary-emulation-plans/
• CALDERA — automated adversary emulation framework from MITRE; runs ATT&CK plans against a target environment
• Atomic Red Team — short, focused technique tests (one ATT&CK technique per "atomic"). Useful for purple-team exercises

The engagement progresses through the kill chain — initial access (for external) or post-foothold execution (for assumed breach), persistence, privilege escalation, defense evasion, credential access, discovery, lateral movement, collection, exfiltration (simulated — see boundaries) — toward the named objective.

Operational notes:

• Every action logged with timestamp, technique, target, and observed effect — for the eventual debrief
• The deconfliction contact answers when the blue team finds the engagement — to pause if escalation risk, to confirm and continue if not
• No destructive techniques unless explicitly authorized — and even then, only against systems that can be safely restored
• Real data is never exfiltrated — use synthetic markers (specific filenames, specific hash values) so blue can verify what was accessed without the team actually moving customer data
• Engagement pauses if the blue team's response would impact real customer service — the engagement is not worth a real outage

Phase 3 — Debrief and reporting

The most under-invested phase, and the one that determines whether the engagement actually improves defenses.

Same-day debrief (within 24 hours of engagement end):

• Red team walks through the timeline of actions
• Blue team walks through what they saw, when they saw it, what they did
• Gaps between the two are the highest-value findings (red did X, blue saw nothing)

Full written report (within 2-4 weeks):

# Red Team Engagement Report
## Engagement: [name]
## Sponsor: [executive sponsor]
## Engagement window: [start - end]
## Engagement type: External / Assumed Breach / Purple
## Authors: [red team leads]

### Executive summary
[3-5 paragraphs — were objectives achieved, what the blue team's detection-and-response posture looks like, top 3-5 systemic recommendations]

### Engagement timeline
[Red-team actions with timestamps and ATT&CK technique IDs]

### Blue-team observations
[For each red-team action, what the blue team saw, when, and how they responded — or did not]

### Detection coverage analysis
[Map of techniques used vs detections that did / should have fired]

### Findings
| ID | Severity | Category | Description |
|----|----------|----------|-------------|

(Categories: Detection gap, Response gap, Privileged-access exposure, Lateral-movement enabler, Crown-jewel access path, Compensating control reliance)

### Per-finding detail
[Technique used, what was achieved, what the blue team did / didn't see, recommended remediation]

### Recommendations
[Prioritized — usually 5-10 items mapping to specific systemic improvements, not point fixes]

### What the engagement did NOT cover
[Honesty about what was out of scope and where coverage gaps remain]

Phase 4 — Improvement and revalidation

Recommendations from the report become work items. The red team's value compounds when:

• High-severity recommendations are tracked to closure (typically: detection rules added per siem-detection, response runbooks updated per soc-operations, control improvements per the audit skills)
• Specific findings are revalidated 6-12 months later, ideally as a purple-team exercise
• Lessons feed breach-patterns and incident-triage runbooks

A red team that finds the same problem twice is a budget that was wasted the second time.

Rules of Engagement (RoE) — what goes in the document

The RoE is the contract. It must be specific.

Boundaries

This is the most consequential boundaries section in this catalog. Read it.

• Authorization is the floor, not the ceiling. A signed authorization does not make every technique acceptable — the contract still bounds what is permitted. When the user is unsure, the answer is "ask the sponsor before proceeding"
• Unauthorized targets are refused. No "hypothetical" engagements against systems the user does not own or control. No "what would you do if" against named third parties. The skill is for authorized engagements, not for adversary-thinking exercises against arbitrary targets
• Destructive techniques are off by default. Even when in-scope, prefer non-destructive alternatives — simulated ransomware (file enumeration without encryption), demonstrated persistence (artifact placement without execution), proof-of-access (read-only)
• Real customer data is not exfiltrated. Use synthetic markers. The blue team verifies what was accessed by what was marked; the red team does not move real data
• Pause for safety. Engagement pauses when real-world impact occurs — outage, data exposure to unauthorized parties, regulatory notification trigger. Restart only after sponsor approval
• Refuse to help build offensive tooling. This skill plans engagements that use existing techniques and tooling responsibly. It does not help write new malware, new C2 frameworks, or new evasion-by-default tooling. Tooling decisions are upstream of this skill
• Refuse to help with social engineering against people who have not consented to be tested. Social engineering can be in-scope, but the targets must be people whose role accepts engagement testing (typically: employees broadly, with explicit exclusions). Refuse if the request is to phish a specific individual outside the consent envelope
• Refuse if the request looks like an internal red team being used to surveil specific employees. Red teams test systems and processes, not people
• Findings are findings, not weapons. A red-team report that produces remediation work is value-positive; one that becomes ammunition in internal politics is value-negative. Authors and reviewers carry responsibility for keeping it the former

References

• MITRE ATT&CK Framework — attack.mitre.org
• MITRE ATT&CK Adversary Emulation Plans — attack.mitre.org/resources/adversary-emulation-plans/
• MITRE CALDERA — automated adversary emulation
• Atomic Red Team — github.com/redcanaryco/atomic-red-team
• TIBER-EU (Threat Intelligence-Based Ethical Red-teaming) — European framework for financial-sector red teaming
• CBEST (UK Bank of England) — UK financial-sector red-team framework
• NIST SP 800-115 (Technical Guide to Information Security Testing and Assessment)
• PTES (Penetration Testing Execution Standard) — methodology source, with red-team-relevant phases
• Red Team Field Manual — Ben Clark — operator-oriented reference
• Adversary Tradecraft and the Importance of Cyber Threat Intelligence — MITRE / CTID writeups
• CTID (Center for Threat-Informed Defense) — ctid.mitre.org — open-source emulation content
• "Red Team Development and Operations" — Joe Vest, James Tubberville
• "How to Hack Like a Ghost" — Sparc Flow (narrative-style; useful for understanding the model of an extended engagement)