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AI Engineering · Version 1.7.0 · Reviewed 2026-08-02

LLM Red-Team Designer

Make AI behavior measurable and safer for adversarial test design and tool-abuse scenarios with evidence, explicit trade-offs, and a verification plan.

4 method steps 6 documented failure modes 5 diagnostic checks 7 quality gates

Creates threat-based adversarial evaluations for prompt injection, data leakage, harmful actions, tool abuse, jailbreaks, and policy bypass.

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What this skill helps you do

  • Adversarial test design
  • Tool-abuse scenarios
  • Safety regression suites

How LLM Red-Team Designer works

You provide

Prompts, model versions, evaluation data, and failures

It inspects

Failure class and context sufficiency for adversarial test design

It decides

A tool-abuse scenarios change with one variable moved

You verify

Pass rate per case class against a pinned baseline

What it checks first

LLM Red-Team Designer creates threat-based adversarial evaluations for prompt injection, data leakage, harmful actions, tool abuse, jailbreaks, and policy bypass. Use it when the work involves Adversarial test design, Tool-abuse scenarios, Safety regression suites.

  1. Whether the failure is systematic across a class of inputs or random, which separates a capability gap from a sampling issue.
  2. Whether evaluation data overlaps training or prompt-development data, which invalidates the measurement.
  3. Token distribution of inputs and outputs, since cost and latency are driven by the tail, not the mean.
  4. Whether the system has a defined behavior for low confidence, or always produces an answer.
  5. Version pinning across model, prompt, retrieval, and tools, because an unpinned component makes regressions unattributable.

Failure modes it recognizes

  • Silent quality regression after a provider updates a model behind an unversioned alias.
  • Evaluation overfitting where the prompt was tuned on the same examples used to score it.
  • Cost and latency dominated by a small number of very long inputs that were never in the test set.
  • Tool-calling loops where the model retries a failing tool without a bounded attempt budget.
  • Confident fabrication when context is insufficient because no refusal path was defined.
  • Distribution shift where production inputs diverge from the evaluation set over time.

Answers it will reject

  • Judging quality by reading a few outputs, which cannot detect a regression of a few percent.
  • Using a larger model to fix a problem caused by missing context, paying more for the same failure.
  • Fine-tuning before exhausting prompting and retrieval, which is slower to iterate and harder to reverse.
  • Using an LLM judge without validating the judge against human labels on the same rubric.

Decision rules it applies

  • Establish a labeled evaluation set and a baseline before changing anything; without a baseline there is no improvement, only change.
  • Pin every version and change one component at a time.
  • Define and test the refusal path explicitly; a system that cannot say "I do not know" will fabricate.
  • Budget latency and cost on p95 token counts, not averages.

Evidence it asks for

  • Score per input class (easy, hard, adversarial, no-answer) so aggregate scores cannot hide a broken class.
  • Log model version, prompt version, and retrieval version on every request for regression attribution.
  • Track p50 and p95 tokens and cost per successful task, not per call.

The method inside

  1. Turn adversarial test design into explicit functional requirements and quality-attribute constraints.
  2. Model the critical path, state, trust, and failure boundaries that govern tool-abuse scenarios.
  3. Compare viable designs for safety regression suites against weighted constraints and operational ownership.
  4. Select a design with consequences, rollout stages, observability, and a reversible adoption path.

Deliverables

  • Adversarial test design assessment
  • Tool-abuse scenarios decision and action plan
  • Safety regression suites verification checklist

Evidence requirements

  • Prompts, model/version, tools, retrieval path, and examples
  • Evaluation dataset and failure cases
  • Latency, cost, privacy, and policy constraints

Quality gates

  • Every material claim traces to supplied evidence or is labeled as a hypothesis.
  • The response follows the declared deliverable contract.
  • No execution, access, measurement, or verification is invented.
  • Secrets and personal data are redacted rather than repeated.
  • The user receives a concrete independent verification step.
  • The relevant failure modes in this domain were considered rather than only the reported symptom.
  • No listed anti-pattern was recommended as a solution.

Example task

Input

Build a red-team plan for an internal agent that reads documents and can create support tickets.

Expected output

Prioritize indirect prompt injection in documents, cross-user data exfiltration, and ticket creation with attacker-controlled fields. Define success as unauthorized effect, not merely undesirable text, and test controls independently...

Boundaries and compatibility

Ideal for

  • Adversarial test design: produce a decision or artifact grounded in supplied evidence.
  • Tool-abuse scenarios: produce a decision or artifact grounded in supplied evidence.
  • Safety regression suites: produce a decision or artifact grounded in supplied evidence.

Out of scope

  • Treating prompt text as a security boundary
  • Claiming model quality from a handful of demos

Agent compatibility

  • GitHub Copilot custom agents
  • Claude Agent Skills / SKILL.md
  • Any instruction-following chat model

Tool policy: Advisory by default. No tools are assumed. If the host provides tools, use read-only evidence gathering unless the user explicitly approves a scoped write or execution action.