The Tool Desk
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Use the questions and acceptance tests below to turn a vague “AI security assessment” into a measurable statement of work for chatbots, retrieval-augmented generation (RAG), tool-calling agents, MCP systems, and multi-agent workflows.
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Start with the system you actually operate
The first buying mistake is choosing a generic test package before describing the production system. Ask the provider to document the system class, trust boundaries, users, tools, integrations, permissions, data stores, model and provider versions, and business-critical actions that will be in scope. The threat model must follow the architecture, not the marketing label.
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| System type | Security questions the engagement must answer |
|---|---|
| Conversational chatbot | Can a user bypass policy controls, extract hidden instructions, obtain another user’s data, or induce unsafe or regulated content? |
| RAG application | Can poisoned or unauthorized documents enter retrieval, cross-tenant data be returned, citations be manipulated, or access filters be bypassed? |
| Tool-calling agent | Can prompts cause unauthorized API calls, excessive permissions, unsafe parameter values, secret disclosure, or actions without required approval? |
| MCP-based architecture | Are server discovery, tool descriptions, authentication, session boundaries, and delegated permissions protected against malicious or confused inputs? |
| Multi-agent workflow | Can one agent escalate privileges, pass untrusted content to another, create an approval loop, or trigger an action outside the intended workflow? |
| Stateful or long-lived sessions | Can memory persist an attack across turns, users, or sessions; can stale context alter later decisions; and can a user erase or inspect retained state? |
Require the provider to state which of these classes it will test and which it will not. “LLM testing” is not a substitute for coverage of tools, memory, identity, workflows, and data stores.
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Write rules of engagement before access is issued
The statement of work should name allowed targets, prohibited actions, test windows, credentials, rate limits, escalation contacts, and stop conditions. Specify whether production, staging, replicas, or synthetic data will be used. Identify business-critical actions that require an approval gate and define what the tester must do if an exploit reaches a real customer record, payment flow, regulated dataset, or external system.
Ask whether the plan includes both single-turn and multi-turn attacks; direct and indirect prompt injection; data exfiltration; unsafe tool use; authorization bypass; harmful-content generation; privacy leakage; bias; reliability failures; and cross-session or memory behavior. Require explicit exclusions rather than assuming that an unmentioned area was tested.
Questions that expose a shallow methodology
How are attacks designed?
Ask whether the team uses custom attack hypotheses derived from your architecture, or only a fixed prompt library. Static prompts can find obvious jailbreaks but may miss workflow bypasses, misuse risks, systemic vulnerabilities, and failures in agentic or tool-enabled systems. The OWASP GenAI Security Project makes this warning explicit in its Vendor Evaluation Criteria for AI Red Teaming Providers & Tooling, Version 1.0, published February 4, 2026 (public PDF release January 13, 2026).
Request a written mapping from each threat hypothesis to the component, identity, permission, data path, and business action it exercises. A useful plan explains why an attack could matter to your organization, not merely that a model produced an undesirable sentence.
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What is automated and what is human-led?
Automation is useful for breadth, mutation, replay, and regression. Human specialists are needed to understand business logic, chain several low-severity weaknesses, validate critical findings, and judge whether a model behavior creates a real authorization or safety failure. Ask for the division of labor, reviewer qualifications, and the point at which a second person verifies a critical result.
How are state and dependencies handled?
For every test, ask what environment state is captured: system prompts, retrieval indexes, policy configuration, tool schemas, identity roles, model and provider versions, dependency versions, and relevant feature flags. Without that snapshot, a later team may be unable to reproduce the result or determine whether a model update fixed it.
How are coverage gaps reported?
Require a coverage matrix listing tested components, attack families, identities, tools, environments, and time windows. Untested areas should be named with the reason: unavailable access, safety restriction, missing telemetry, or deliberate exclusion. A percentage without its denominator is not a meaningful coverage metric.
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Demand evidence, not a slide deck
Review a redacted report before signing
Ask for a sample redacted report and one anonymized finding walkthrough. The walkthrough should show the attack sequence, affected component, evidence, exact reproduction steps, severity rationale, business impact, confidence, remediation, and retest result. If the provider cannot show these elements because of client confidentiality, ask for a synthetic example with the same level of detail.
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| Evidence to request | What good evidence looks like | Why it matters |
|---|---|---|
| Attack transcript | Complete prompts, model outputs, tool calls, identities, timestamps, and relevant state | Allows an engineer to reproduce the behavior instead of trusting a screenshot |
| Component attribution | Clear identification of the model, application layer, retrieval service, tool, policy, or integration involved | Prevents remediation from being assigned to the wrong team |
| Severity and confidence | Separate ratings with written criteria and uncertainty notes | Distinguishes probable business harm from an intriguing but unverified behavior |
| Business-impact mapping | Specific affected asset, user, process, regulatory exposure, or financial consequence | Gives owners a defensible remediation priority |
| Human verification | Named review step for critical or high-impact findings | Reduces false positives and misinterpreted model output |
| Regression artifact | Reusable prompt, test harness, expected result, and pass/fail condition | Lets your team run the test after fixes and model changes |
Ask how false positives are reduced
Find out whether a finding must be reproduced more than once, in more than one session, or by an independent reviewer. Ask how the team handles nondeterministic model output, safety filters that change between runs, and attacks that work only under a particular temperature, context length, or tool state. A confidence score should explain what was observed and what remains uncertain; it should not disguise uncertainty as a precise-looking number.
Require novel tests and reusable tests
Ask for examples where custom testing produced a finding that a standard library would not have found. Also require delivery of attack prompts and outputs as regression tests, subject to redaction of secrets and personal data. A one-time demonstration has little value if your engineers cannot rerun it after a prompt, model, dependency, or tool change.
For agentic testing, prove the safety controls live
Autonomous testing can create real side effects. Documentation alone cannot establish that an agent will stop, stay within scope, or respect an approval boundary. Require a live demonstration or customer acceptance test of every control that limits autonomy.
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- Kill switch: Show the exact action that stops active runs and prevents queued actions from executing.
- Independent termination paths: Demonstrate at least two ways to stop testing, such as a customer-admin control and an infrastructure-level control.
- Scope enforcement: Attempt an out-of-scope target and show that the system blocks it before the request reaches the target.
- Rate limiting: Verify limits for requests, tool calls, token use, and concurrent sessions.
- Approval gates: Test that sensitive actions pause for an authorized human and cannot be approved by the agent itself.
- Credential controls: Use least-privilege, time-limited credentials and show how they are rotated or revoked.
- Emergency escalation: Identify who is contacted, by which channel, and within what time when a test causes an unexpected effect.
- Customer removal authority: Confirm that you can disable deployed agents or integrations without waiting for vendor cooperation.
Record the observed stop time, blocked action, alert, and evidence produced during the demonstration. The OWASP APTS guide specifically treats behavioral requirements such as kill-switch timing and scope enforcement as controls that cannot be fully verified through paperwork.
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Use APTS tiers as an assurance ladder
| OWASP APTS tier | Cumulative requirements | Intended assurance level |
|---|---|---|
| Tier 1 — Foundation | 72 | Baseline controls for a foundational deployment |
| Tier 2 — Verified | 157 | Recommended minimum for production deployments, regulated industries, or engagements requiring full accountability |
| Tier 3 — Comprehensive | 173 | For critical infrastructure, fully autonomous operations, and the strictest regulatory requirements |
These counts reflect the current OWASP APTS guide accessed in 2026. Ask the provider to identify the tier its platform or service can evidence, which requirements are in scope, and which remain unverified. Do not treat a tier label as proof unless the underlying controls are demonstrated in your environment.
Put data, logs, and model changes in the contract
Security and privacy terms belong in the statement of work and security addendum, not in an informal email. Your contract should answer the following questions in operational language.
Logging and replay
- What is logged for every action, decision, tool invocation, timestamp, input, output, and outcome?
- Are logs tamper-evident, cryptographically chained or signed, and independently verifiable?
- Can a finding be replayed with the environment state captured at test time?
- Who can access raw prompts, outputs, secrets, and personal data in the logs?
- How are redactions recorded so that an auditor knows what was removed?
Model, prompt, and dependency drift
- How are model, system-prompt, policy, dependency, retrieval-index, and tool-schema changes recorded?
- What happens when a provider silently changes a hosted model during the engagement?
- Will the team rerun critical tests after a material change, and what event triggers that rerun?
- How are findings re-scored when a compensating control changes exploitability or impact?
Isolation and processing location
- How are customer tenants isolated in storage, processing, logs, and support access?
- Where is data processed and stored, including backups and temporary worker environments?
- Which third-party models or services receive prompts, outputs, files, or telemetry?
- Are customer inputs used to train or tune any provider or third-party model?
Retention, deletion, and credentials
- What are the retention periods for prompts, outputs, logs, reports, screenshots, and evidence archives?
- What secure-disposal procedure applies at expiration or termination?
- Will the provider issue a deletion certificate covering primary storage, replicas, and backups where technically possible?
- What is the credential-revocation sequence, and how quickly must it occur after the engagement?
Incident notification and handoff
- What event qualifies as an incident, and what notification deadline applies?
- Who receives the first notification, including an after-hours contact?
- Are reports and evidence encrypted at handoff and protected in ticketing integrations?
- Which party owns discovered secrets, regulated data, and remediation records?
Red flags include no kill-switch demonstration, no customer access to audit trails, vague AI-model governance, no data-isolation explanation, no credential-rotation process, and no incident-notification timeline.
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Define the report and retest before testing starts
Minimum report contents
Make these deliverables contractual: an executive summary; a technical methodology; a scope and coverage matrix; attack evidence; reproduction steps; severity and confidence for each finding; business-impact mapping; remediation guidance; a list of untested areas; and a retest record. Require findings to identify the affected component and the assumptions needed to reproduce them.
Separate severity from confidence
Severity describes potential harm if the weakness is real and exploitable. Confidence describes how strongly the evidence supports the finding. A high-severity, low-confidence hypothesis should be investigated differently from a high-severity, high-confidence exploit. Ask for written scoring criteria, not only colored labels.
Make retesting measurable
Define a retest as a new execution against the changed system, not a desk review of a developer’s ticket. Specify the test cases, environment, evidence required, pass/fail rule, and delivery deadline. State whether unresolved findings are re-scored after compensating controls, and who decides that the control is effective. Include how many retest cycles are covered and what happens when a fix introduces a new path to the same impact.
Use independent frameworks as acceptance anchors
NIST ARIA: three complementary modes
The NIST ARIA Evaluation Planning Manual (NIST AI 200-3, published September 18, 2026) describes holistic evaluation through three modes: Model Testing, Red Teaming, and User Testing. Use this structure to prevent a red-team engagement from being mistaken for the entire assurance program. Model testing can examine defined capabilities and failure modes; red teaming probes adversarial behavior in context; user testing examines how people actually interpret and use the system.
Ask the provider to state which ARIA mode its work covers, what evidence it produces, and which modes must be supplied by your internal teams or another evaluator.
OWASP AISVS: a testable requirements catalogue
OWASP AISVS is a vendor-neutral, free catalogue of testable security requirements for AI-enabled systems. Use it as a baseline for acceptance tests, penetration tests, red-team exercises, and audits. Map each in-scope requirement to evidence, an owner, and a pass/fail condition. A mapping that merely lists requirement numbers without test results is not an assessment.
Compare providers on scope-linked value
When two or more proposals remain, compare equivalent deliverables rather than headline day rates. No authoritative market price is established for this category, so request an itemized statement of work with assumptions, exclusions, staffing, retests, and expenses.
| Comparison axis | Questions to put side by side |
|---|---|
| System and threat-model coverage | Does the proposal cover your RAG, tools, MCP servers, agents, memory, identities, and business actions? |
| Human expertise versus automation | Who designs attacks, reviews critical findings, and interprets business impact? |
| Reproducibility | Are complete transcripts, state snapshots, and regression tests delivered? |
| Stateful and agentic depth | Are multi-turn, cross-session, tool-chain, and approval-boundary attacks included? |
| Safety controls | Can your operators stop testing, enforce scope, revoke credentials, and remove agents? |
| Evidence and reporting | Are confidence, severity, coverage gaps, and remediation acceptance criteria explicit? |
| Data governance | Are residency, isolation, third-party model access, retention, deletion, and notification defined? |
| Independence | Does the evaluator have incentives or implementation responsibilities that could bias findings? |
| Remediation and retest | How many retest cycles are included, and how are compensating controls scored? |
| Standards mapping | Can the work map to NIST ARIA modes and OWASP AISVS or APTS requirements? |
| Deployment model | Is the platform hosted, deployed in your environment, or operated as a controlled service? |
| Total scope-linked cost | What are the fees for setup, access, custom tooling, travel, retesting, storage, and overages? |
Reject proposals that make direct price comparisons impossible by hiding testing volume, architecture coverage, analyst time, or retest obligations.
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A practical pre-signing workflow
- Prepare an architecture brief. List models and versions, data flows, identities, tools, integrations, memory, environments, business-critical actions, and regulatory constraints.
- Issue the same question set to every provider. Require written scope, exclusions, rules of engagement, methodology, safety controls, deliverables, and assumptions.
- Inspect evidence. Review a redacted report and walkthrough, then verify reproducibility, human review, confidence scoring, and regression-test delivery.
- Run the safety acceptance test. Demonstrate kill-switch timing, scope blocking, rate limits, approval gates, credential revocation, and emergency escalation before autonomous access is granted.
- Negotiate the data addendum. Set processing locations, tenant isolation, third-party model access, retention, deletion proof, incident notification, and log access.
- Lock down retesting. Define pass/fail criteria, evidence, included cycles, deadlines, and re-scoring rules for compensating controls.
- Approve against an independent anchor. Map deliverables to the relevant NIST ARIA modes and OWASP AISVS requirements; use APTS tiers to describe assurance for autonomous testing.
- Sign only an itemized scope. The final document should identify targets, attack classes, identities, tools, windows, staffing, outputs, exclusions, price, and change-control procedure.
Deal-breakers that should stop procurement
- The provider promises a “jailbreak score” but cannot describe business workflows, tools, permissions, or data paths.
- The methodology is only a static prompt list with no custom attack design or multi-turn testing.
- Critical findings are not independently verified, reproducible, or tied to a specific component.
- Coverage gaps are omitted, and the provider treats untested areas as secure.
- An autonomous platform cannot demonstrate a kill switch, scope enforcement, rate limits, approval gates, or customer-controlled credential revocation.
- Logs cannot be accessed, verified, or replayed with the original environment state.
- The contract is silent on third-party model access, tenant isolation, retention, deletion proof, or incident notification.
- Retesting is described as “included support” without test cases, pass/fail criteria, evidence, or a deadline.
- The proposal supplies a headline day rate but no itemized scope from which competing bids can be compared.
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