Purple Team & Adversary Emulation

Purpose

Enable Claude to plan and run purple team engagements: red and blue working the same ATT&CK techniques together so that every emulated behavior produces a measured answer to "did we see it, and could we have stopped it?" The deliverable is not a compromise — it is a validated, quantified improvement in detection and prevention coverage.

This skill sits between Skill 14 (Red Team — how to execute the offensive TTPs) and Skills 15/12/11 (Blue Team, SIEM/Sigma, SOC — how to detect and respond). It supplies the collaborative loop and the coverage measurement that turn one-off findings into durable detections.

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⚠️ Authorization Gate — Read First

Adversary emulation executes real attack techniques against real systems. Before providing operational assistance (test execution, payloads, C2, live-fire steps), confirm:

[ ] Written authorization naming the systems/environment in scope exists and is current
[ ] Scope, allowed techniques, and explicit exclusions (fragile prod, safety systems, OT) are defined
[ ] A deconfliction channel and point of contact are agreed with the SOC/blue team
[ ] A stop/abort procedure and rollback plan are documented and understood
[ ] Destructive or availability-impacting techniques are excluded unless separately authorized
[ ] Test data/accounts are used; no real user data is exfiltrated

If authorization cannot be confirmed, restrict assistance to planning, coverage analysis, detection engineering, and tabletop emulation — which need no live execution — and say so explicitly. Never provide live-fire steps against systems the user cannot show authorization for. For the offensive tradecraft itself, defer to Skill 14's Rules of Engagement.

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Activation Triggers

This skill activates when the user asks about:

• Planning a purple team engagement, adversary emulation plan, or breach-and-attack-simulation exercise
• Choosing and emulating a specific threat actor's TTPs (from CTI / ATT&CK groups)
• Atomic Red Team, MITRE CALDERA, CTID Adversary Emulation Library, or MITRE Engenuity ATT&CK Evaluations
• The detect → tune → re-test validation loop for a technique
• Measuring or visualizing detection coverage (ATT&CK Navigator layer, DeTT&CT, heatmap)
• Detection maturity per technique (none / telemetry / detection / prevention)
• Deconfliction between red and blue, or safe execution of attack techniques
• Purple-team metrics — MTTD/MTTR, detection rate, per-technique time-to-detect, gap backlog

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Prerequisites

python3 --version          # 3.10+; standard library only for the core script
pip install pyyaml         # optional — only to load emulation plans written in YAML

Optional enhanced tooling:

• Atomic Red Team — library of small, ATT&CK-mapped tests
• MITRE CALDERA — automated adversary emulation platform
• CTID Adversary Emulation Library — full actor emulation plans
• DeTT&CT — data-source and detection coverage scoring
• ATT&CK Navigator — coverage heatmaps
• VECTR — purple-team assessment tracking

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Core Capabilities

1. Engagement Model Selection

Pick the collaboration model that fits the maturity and goal:

• Tabletop emulation — walk the actor's kill chain on paper; verify each step would generate telemetry and should fire a detection. No execution; safe anywhere, ideal first pass.
• Micro-emulation — a handful of atomic tests for a specific technique or a newly deployed detection. Fast feedback, small blast radius.
• Full-campaign emulation — end-to-end emulation of a named actor across the kill chain, run collaboratively with the SOC watching in real time. Highest fidelity, highest coordination cost.
• Continuous / automated (BAS) — scheduled automated tests to catch detection regressions over time.

Default to the least invasive model that answers the question, and escalate only with cause and authorization.

2. Threat-Informed Emulation Planning

When the user asks to plan an emulation:

1. Choose the adversary from intelligence, not convenience. Pull the actor/campaign relevant to the org's sector and crown jewels (hand-off from Skill 21 CTI / Skill 06). Prefer an actor the org actually faces.
2. Build the technique list by walking the actor's known TTPs across ATT&CK tactics (Initial Access → Impact). For each, capture: technique ID, tactic, a concrete procedure, the expected data source/telemetry, and the expected detection.
3. Order by kill chain and set objectives — what "success" means for each step (e.g., "Kerberoast a service account" → objective: SOC alerts within N minutes).
4. Map to a test source — an Atomic Red Team test, a CALDERA ability, or a documented manual procedure — so execution is repeatable.
5. Record the plan as structured data (scripts/detection_validator.py reads a JSON/YAML plan) so results are trackable across re-tests.

3. The Detect–Tune–Validate Loop

For every technique, run the collaborative loop and record the outcome:

Execute technique (red, announced to blue)
        ↓
Confirm telemetry exists  ──no──▶ GAP: missing data source  → Skill 15 (onboard log source)
        ↓ yes
Confirm a detection fires  ──no──▶ GAP: no detection         → Skill 12 (write Sigma) / Skill 15
        ↓ yes
Was it prevented?          ──no──▶ note: detect-only          → hardening backlog → Skill 15
        ↓
Measure time-to-detect, tune false positives, re-test to confirm the fix

Classify each technique's outcome on this ladder: none (no telemetry) → telemetry (data exists, no alert) → detection (alert fires) → prevention (blocked). The gap between telemetry and detection is where most purple-team value is realized.

4. Coverage Measurement & Visualization

1. Score every in-scope technique on the none/telemetry/detection/prevention ladder and compute coverage per tactic and overall.
2. Produce an ATT&CK Navigator layer (technique IDs colored by coverage) so the heatmap is shareable and diff-able across engagements.
3. Track drift — compare this engagement's layer to the last one; a technique that regressed from detection→telemetry is a finding.
4. Avoid the coverage-theater trap — a technique "covered" by one brittle, high-false-positive rule is not covered. Weight robustness and note single-signature dependencies.
5. Use scripts/detection_validator.py to turn a results plan into a per-tactic coverage matrix, a Navigator layer, MTTD statistics, and a prioritized gap list.

5. Safe Execution & Deconfliction

• Announce every action to the blue team in the agreed channel with a timestamp, so a real intrusion during the exercise is not mistaken for the test (and vice versa).
• Bound the blast radius — test accounts, test data, non-production or clearly-scoped hosts; never destructive/availability-impacting techniques without separate sign-off (see Skill 18 for OT/ICS where impact can be physical).
• Have an abort — a single agreed signal that stops all offensive activity, plus a rollback for any change made.
• Log everything — command, time, operator, target, expected vs. observed — so results are attributable and repeatable.

6. Metrics & Reporting

Report outcomes, not activity:

• Detection rate — % of executed techniques that fired a detection; prevention rate — % blocked.
• MTTD / MTTR — mean time to detect / respond, per technique and overall; call out the slowest.
• Coverage delta — improvement vs. the previous engagement.
• Remediation backlog — each gap as an actionable item (missing log source, new detection to write, hardening change) with an owner and priority, handed to Skills 15/12/11.

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Output Template

# Purple Team Engagement Report
**Engagement:** [Name]  |  **Date:** [YYYY-MM-DD]
**Emulated adversary:** [Actor / campaign]  |  **Model:** [Tabletop / Micro / Full-campaign / BAS]
**Authorization:** [reference]  |  **Deconfliction POC:** [name/channel]

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## Executive Summary
[2–3 sentences: techniques run, detection rate, prevention rate, top gap, coverage delta.]

## Coverage Scorecard
| Metric | Result |
|--------|--------|
| Techniques executed | N |
| Detected | N (xx%) |
| Prevented | N (xx%) |
| Mean time-to-detect | mm:ss |
| Coverage delta vs. prior | +/- x techniques |

## Per-Technique Results
| Tactic | Technique (ID) | Executed | Data source | Outcome | TTD | Detection / Gap |
|--------|----------------|----------|-------------|---------|-----|-----------------|
| Credential Access | Kerberoasting (T1558.003) | ✅ | Security 4769 | detection | 04:12 | Sigma: rc4 TGS request |
| Defense Evasion | Clear Windows Event Logs (T1070.001) | ✅ | Security 1102 | telemetry | — | GAP: no alert on 1102 |

## Coverage Heatmap
[ATT&CK Navigator layer attached: `navigator_layer.json`]

## Prioritized Remediation Backlog
| Priority | Gap | Action | Owner | Handoff |
|----------|-----|--------|-------|---------|
| High | No alert on log clearing | Write Sigma for EID 1102 | Detection Eng | → Skill 12 |
| Med | RDP lateral movement detect-only | Add prevention control | Blue Team | → Skill 15 |

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Script Reference

detection_validator.py

# Score an emulation results plan: coverage matrix, MTTD, gaps
python scripts/detection_validator.py --plan results.json

# Also emit an ATT&CK Navigator layer and a JSON report
python scripts/detection_validator.py --plan results.json \
    --navigator navigator_layer.json --output report.json

# Compare against a previous engagement to compute coverage drift
python scripts/detection_validator.py --plan results.json --baseline prior.json

# Self-contained demo with a built-in sample emulation plan
python scripts/detection_validator.py --demo

A plan is a JSON (or YAML with pyyaml) list of test entries — technique_id, technique, tactic, executed, data_source, outcome (none/telemetry/detection/prevention), and optional time_to_detect_seconds. The script computes per-tactic and overall coverage, detection/prevention rates, MTTD, a prioritized gap list, and an ATT&CK Navigator layer. Scoring reflects only what the plan records — it validates your results, it does not execute anything.

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Skill Integration

Condition	Next Skill
Which adversary/TTPs to emulate	← Skill 21 (CTI) and Skill 06 (Threat Hunting)
Executing the offensive techniques	→ Skill 14 (Red Team Operations) — under its RoE
A gap needs a detection written	→ Skill 12 (Log Analysis / Sigma)
A gap needs a hardening/prevention control	→ Skill 15 (Blue Team Defense)
Validating SOC alerting/triage in the loop	→ Skill 11 (CSOC Operations)
Emulation touches OT/ICS environments	→ Skill 18 (OT/ICS) — safety-first, non-disruptive only
A real incident is discovered mid-exercise	→ Skill 07 (Incident Response) — declare and deconflict

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References

• MITRE ATT&CK · ATT&CK Navigator
• Center for Threat-Informed Defense — Adversary Emulation Library
• Atomic Red Team (Red Canary)
• MITRE CALDERA
• DeTT&CT — Detect Tactics, Techniques & Combat Threats
• MITRE Engenuity ATT&CK Evaluations
• VECTR (Security Risk Advisors)
• Sigma — Generic Detection Rule Format
• Scott Roberts / Robert M. Lee — Intelligence-Driven Defense