Red Teaming

Red Teaming

Core principle: Assume the system will be attacked, gamed, or stressed by an intelligent adversary. Think like the attacker. Find weaknesses before they're exploited.

Red Team Mindset

Actively try to break the system, not validate it.

• Hostile intent — How would a bad actor abuse this?
• Assume failure — Start from "this has failed" — what enabled it?
• Partial information — What does the adversary know that defenders don't?
• Creativity — Attackers aren't constrained by intended use
• Asymmetry — Defenders protect everything; attackers need one opening

Red Team Dimensions

1. Technical Attack Surface

• Inputs that could be manipulated
• Assumptions about data validity
• Edge cases, limits, unexpected inputs
• Trust boundaries — can they be crossed?
• Failure under load, partial failure, poisoned input

2. Incentive & Game Theory

• Who has incentive to game/subvert this?
• What does the incentive structure actually reward (vs. intends to)?
• Maximum-extraction / minimum-contribution path?
• Collusion risks between actors?

3. Process & Human

• Reliance on human judgment, discipline, vigilance
• Social engineering vectors
• Insider acting against the system
• Process ambiguity enabling inconsistent/exploitable behavior

4. Assumption Attacks

• What must be true — and what if each is false?
• Information asymmetry between parties
• Dependencies that could be weaponized

5. Cascade & Systemic

• Single failure that propagates most widely
• Highest-impact, lowest-effort attack
• What a sophisticated attacker would do that a naive one wouldn't
• Kill chain — sequence to catastrophic failure

Output Format

Attack Surface Map

• Entry points (inputs, interfaces, dependencies)
• Trust boundaries (one actor's output → another's input)
• High-value targets

Top Attack Scenarios

For each:

• Name | Actor (external/insider/automated/accidental) | Method | Impact (CIA + reputation/financial) | Likelihood (L/M/H) | Current defenses | Defense gaps

Highest-Risk Findings

Ranked: (Likelihood × Impact) / Existing Defenses. Top 3 to fix first.

Kill Chain Analysis

For the most critical scenario:

[Initial access] → [Lateral movement] → [Exploitation] → [Impact]

At each step: what stops the attacker? what's missing?

Hardening Recommendations

For each high-risk finding:

• Short-term — reduce exposure now, even imperfectly
• Long-term — eliminate or fundamentally reduce the surface
• Detection — if prevention fails, how do we know?

Red Team Questions by Domain

Software / Architecture

• Malformed, empty, enormous, or adversarial input?
• Dependency returns unexpected data or fails silently?
• Two requests race?
• Credential or token leaked?
• Component compromised from within?

AI / Agent Systems

• Prompt injection in input?
• Context poisoned by a prior step?
• Tool the agent calls is compromised or returns false data?
• Agent asked to act outside intended scope?
• Two agents give conflicting instructions to a third?

Product / Business

• User extracts value without paying?
• User reverse-engineers to game metrics?
• Competitor copies model and undercuts?
• Key partner defects or changes terms?
• Regulatory conditions change?

Organization / Process

• Key person leaves?
• Incentives push people to hide info from each other?
• Process followed to the letter but not the spirit?
• Deadline pressure causes safeguards to be skipped?

Levels of Depth

Asymmetric Paranoia

The red team doesn't need every flaw — it needs the one that matters most. Always prioritize: highest-impact attack that currently has no defense.