Thinking Red Team

Red Team Thinking

Overview

Red teaming is adversarial security review: deliberately attacking a system you control to find vulnerabilities before an attacker does. This skill is scoped to security/code vulnerability detection — it is NOT for plan stress-testing or decision challenge (use thinking-pre-mortem or thinking-steel-manning for those).

The anti-fabrication gate is the most important rule: every reported finding MUST include a concrete, reproducible attack path — entry point → exact steps → realized impact. If you cannot describe how the attack actually executes against this code/config, it is not a finding. Drop it. A short report of real, demonstrable vulnerabilities beats a long list of speculation.

Core Principle: Attack yourself before others do. But only report what you can actually break.

When to Use

• Security review of code, authentication, authorization, APIs, or infrastructure you control
• Pre-launch security hardening of a system that handles auth, data, or money
• Evaluating whether a specific vulnerability class (injection, XSS, auth bypass, etc.) is present in your code

Decision flow:

Reviewing a system for security?
  → Can you demonstrate an attack path? → No → Don't report it
  → Is the finding reproducible against this code/config? → No → Drop it
  → Is this plan stress-testing or decision challenge? → Yes → Use thinking-pre-mortem or thinking-steel-manning
  → No → RED TEAM IT

When NOT to Use

• Speculative claims without a reproducible attack path. This is the anti-fabrication gate. "Best practice says X" or "this could theoretically be vulnerable" is not a finding. State the entry point, exact steps, and realized impact — or drop it.
• Plan, strategy, or decision stress-testing. For "how could this plan fail," use thinking-pre-mortem. For "what's the strongest case against this decision," use thinking-steel-manning.
• Architecture review without security focus. For architecture resilience, use thinking-systems or thinking-pre-mortem.
• Running scanners replaces thinking. Where you can actually run a SAST tool, fuzzer, or PoC, do that. This skill structures the adversarial thinking; it doesn't replace automated verification.
• Padding the report to look thorough. A short list of real vulnerabilities beats a long list of theoretical ones. Resist the incentive to add "informational" or "best-practice" items.

Procedure

Step 1: Define the Target and Scope

Target: [System/component under review]
Scope: [What to attack — be specific]
Out of scope: [What to skip]
Goal: [What constitutes a successful attack — e.g., unauthorized access, data exfiltration, privilege escalation]

Step 2: Adopt the Adversary Mindset

Identify who would attack this system and what they want:

Adversary profiles:
- External attacker (no access): targets public endpoints, auth bypass, injection
- Authenticated user (basic access): targets privilege escalation, IDOR, business logic
- Insider (elevated access): targets data exfiltration, audit bypass

For each profile, ask: "If I wanted to cause maximum damage with their access level, how would I?"

Step 3: Enumerate the Attack Surface

Map every entry point and trust boundary:

Step 4: Execute Attack Scenarios

For each attack surface, attempt to break the system:

Attack: Credential stuffing against login
Steps:
1. Obtain breach database of known credentials
2. Script requests against /login with varied credentials
3. Observe rate limiting, account lockout, timing differences
Findings:
- Rate limiting: 10 req/min per IP (bypassable via distribution)
- Account lockout: none
- Timing: response time reveals valid vs invalid usernames ← VULNERABILITY

For each attack scenario, record: the entry point, exact steps taken, observed behavior, and whether a vulnerability was found.

Step 5: Attempt Defense Bypass

For each defense encountered, try to bypass it:

Step 6: Document Findings — With the Anti-Fabrication Gate

For EVERY finding, fill out:

Finding: [Title]
Severity: Critical / High / Medium / Low
Attack path (REQUIRED):
  Entry point: [URL, endpoint, parameter, file]
  Steps: [1. Send X, 2. Observe Y, 3. Escalate to Z]
  Realized impact: [What the attacker actually achieves — data access, privilege, DoS]
Remediation: [Concrete fix]

If you cannot fill out the attack path completely, drop the finding. Do not report "Missing HttpOnly flag" as a standalone finding without demonstrating session token theft. Do not report "No rate limiting" without demonstrating a viable brute-force attack.

Output Contract

A completed Red Team report produces:

1. Target and Scope — what was reviewed and what was excluded 2. Attack Surface Map — entry points with exposure levels and trust boundaries 3. Attack Scenarios Executed — each scenario with steps, observations, and outcome 4. Findings Report — each with severity AND a concrete, reproducible attack path (entry point → steps → impact) 5. Defense Bypass Results — which defenses held and which were circumvented 6. Remediation Recommendations — prioritized by severity with concrete fixes

Findings without a complete attack path are excluded from the report. A report with zero findings is acceptable if no reproducible vulnerabilities were discovered.

Anti-Patterns