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Choose an AI security assessment provider by how well its proposed work matches your system’s architecture and business risks—not by a generic promise to “red-team AI.” Before comparing bids, define what must be assessed, what the provider is authorized to do, and what evidence and remediation you expect. Then compare providers against the same scope, safety rules, testing approach, reporting requirements, and follow-up plan.
Define what you need assessed before asking for proposals
A provider cannot produce a meaningful assessment from a product label alone. “AI assistant,” for example, does not tell a tester whether the system can retrieve confidential records, call external tools, change account data, or pass information between agents. Start with a practical inventory and a clear statement of the business outcomes you need the assessment to support.
Map the system and its boundaries
Document the components that can affect the AI system’s security or the consequences of its output. Include the model or models, user-facing interfaces, retrieval-augmented generation (RAG) sources, connected tools, agent actions, integrations, sensitive data, user groups, and business-critical workflows. Note how the system is deployed and used in its operating context, including any relevant staging or production environment boundaries.
For each component, specify whether it is in scope, out of scope, or in scope only under particular conditions. A scope statement should make it possible for a provider to say exactly what it will test and what it will not. If you do not yet know which components or workflows matter most, say so in the request for proposal (RFP) and ask the provider to identify assumptions and propose a discovery step.
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Describe the risks that matter to your business
Connect the system inventory to potential harm. Consider, for example, whether an attacker or an ordinary user could obtain information they should not see, misuse a connected tool, cause an unsafe or unauthorized action, or disrupt a business-critical workflow. These are prompts for scoping—not a complete or universal threat list. The relevant abuse cases depend on your architecture, data, users, and business logic.
State which workflows and assets are most important, what kinds of misuse would have serious consequences, and what the assessment is meant to help you decide. That context lets providers propose tests that exercise your actual system rather than demonstrate a handful of generic prompt attacks.
Get written authorization and rules of engagement
Before testing begins, agree in writing on the authorized targets, boundaries, test accounts, environment, permitted techniques, prohibited actions, approval gates, escalation contacts, data handling, and conditions for pausing or stopping work. Be explicit about destructive actions or other behavior that must not be attempted. Unclear authorization and unsafe testing are reasons to reject or revise a proposal, not minor administrative issues.
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OWASP’s provider evaluation criteria and AI red-teaming guide treat scope, realistic threat models, safe testing, and authorization as important parts of provider evaluation.
Check whether the proposed tests fit your AI architecture
Different designs create different attack surfaces. A chat interface, a RAG application, a tool-calling agent, and a multi-agent workflow should not automatically receive the same test plan. Ask the provider to explain how its methods change based on your architecture and business logic, and what it will examine beyond prompts and model responses.
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For a chatbot or other user-facing interface
Ask what the provider will test about the interface’s behavior, the information it can access, and how it responds to attempts to elicit unsafe or unauthorized behavior. A prompt-focused exercise may be part of an assessment, but do not treat a demonstration of jailbreak prompts as a substitute for examining the application, its data access, and its business rules.
For RAG and other systems connected to information sources
Ask how the proposed work covers the retrieval pipeline and the sources it can reach. The provider should be able to explain which data stores and access paths are in scope, how it will assess whether information is exposed inappropriately, and what evidence it will collect. The answer should reflect your actual configuration rather than assume that all RAG systems have the same risks.
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If an AI system can call tools or take actions, ask how the provider will assess the actions it can perform, the systems it can reach, and the conditions under which it may act. Make clear which tools and integrations are authorized for testing and which actions are prohibited. Require the provider to explain how it will test for unsafe or unauthorized behavior without exceeding the agreed boundaries.
For multi-agent workflows
Ask the provider to account for the workflow as a whole: which components exchange information, what actions are available at each point, and where relevant business rules apply. A plan that examines only an isolated prompt or one agent may not address the risks created by the system’s connections and handoffs. Have the provider identify the parts it will cover and any parts it will not.
Look for combined human and automated testing
Ask how manual adversarial work and automated tools will be used together, what each contributes, and how the provider will investigate a result before reporting it as a finding. OWASP’s guide says automation should reduce cost and working hours without eliminating human adversarial creativity. A proposal should explain how that principle applies to your scope rather than presenting automation as proof of coverage.
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Use standards to make proposals comparable—not as a quality guarantee
Frameworks can help buyers organize requirements and ask providers to show their work. They do not, by themselves, establish that a provider is qualified or that a particular assessment is complete.
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OWASP AISVS
The OWASP Artificial Intelligence Security Verification Standard (AISVS) provides testable AI-specific requirements covering security design, development, deployment, monitoring, and retirement. The OWASP Foundation’s AISVS 1.0 page, which reports a June 2026 release, lists 191 requirements across 12 chapters and three appendices. Each requirement has a verification level of 1, 2, or 3. The standard is vendor-neutral and free to use.
Ask providers to map relevant test cases and findings to AISVS requirements, explain which requirements apply, and identify any that are out of scope. AISVS can support penetration tests, red-team exercises, audits, and procurement. It does not replace general application, infrastructure, or supply-chain security work; OWASP says those areas should be addressed in parallel. Check the current AISVS documentation and agree on the version and requirements that will govern the engagement.
NIST AI RMF
The NIST AI Risk Management Framework (AI RMF) is a voluntary framework for incorporating trustworthiness considerations into the design, development, use, and evaluation of AI products, services, and systems. NIST released AI RMF 1.0 on January 26, 2023, and describes it as being revised. It is a risk-management framework, not a vendor certification.
Ask how the provider will connect assessment activities and outcomes to your risk-management process or relevant AI RMF outcomes. At the time of procurement, verify which edition or newer profile applies to your organization; do not assume a proposal that names the framework is using the current version or has completed a specific certification.
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AI testing methods and metrics
NIST’s AI Metrology Center supports the selection of methodologies and metrics for testing, evaluation, verification, and validation (TEVV). Its resources can help inform a discussion about how a provider will measure and evaluate results. NIST explicitly cautions that inclusion of a methodology, metric, or tool in the center is not an endorsement, validation, or determination of suitability. Ask why a proposed method fits your system and what its limits are.
Send every provider the same RFP questions
A common RFP makes it easier to distinguish a tailored plan from a generic service description. Give each candidate the same system summary, scope boundaries, constraints, and deliverable expectations. Ask each to answer the following points in writing.
Scope and fit
- Which models, application components, RAG sources, agent tools, integrations, data, users, and workflows are included?
- What is excluded, and what assumptions could change the proposed scope or results?
- How will the plan address business logic and conventional application or security controls alongside AI-specific tests?
- Which discovery questions must be resolved before testing can start?
Threat model and test method
- What realistic abuse cases will the provider test, and how were they selected for this system?
- How will the work go beyond prompt-only jailbreak demonstrations?
- How will manual adversarial work and automation be combined?
- How will the team determine whether a potential issue is reproducible and relevant to the agreed scope?
- What coverage limitations should the business expect?
Framework mapping
- Can the provider map applicable tests and findings to OWASP AISVS, relevant OWASP AI guidance, NIST AI RMF outcomes, or your own control set?
- Which version of each framework will the provider use?
- How will it handle requirements that do not apply or cannot be tested under the agreed scope?
Authorization and safety
- What written authorization and rules of engagement does the provider require?
- What boundaries, approval gates, test accounts, and sandbox expectations will it document?
- Which destructive or otherwise prohibited actions will it avoid?
- Who are the escalation contacts, what are the stop conditions, and how will data be handled?
People, review, and independence
- Who will perform the work, and what relevant experience will they bring to your system type and assessment scope?
- How will the work and findings receive quality review?
- Does the provider have a product or implementation relationship that could affect the independence of the assessment, and how will it address that possibility?
These are procurement questions, not proof that a particular credential or provider has been independently certified. A proposal should name the people responsible and explain how their experience relates to the planned work. If it does not, ask for clarification before treating the firm’s general capabilities as a substitute for the team you will actually receive.
Evidence and closeout
- Can the provider share a redacted sample report?
- Will each finding identify affected components, reproducible evidence, conditions, and relevant limitations?
- How will the provider explain severity and business impact?
- Will the report prioritize remediation and identify recommended retesting?
- What are the final deliverables, and who will receive them?
Cost and follow-up
- What work, deliverables, remediation support, and retesting are included in the price?
- What scope assumptions could change the cost or timeline?
- What support is available when your team needs to interpret findings or confirm a fix?
Compare the total proposed engagement against its actual scope, outputs, and follow-up—not day rates alone. OWASP’s guide says costs should correlate with measurable risk reduction, clear reporting, and prioritized remediation guidance. A lower quote may leave important components or useful closeout work out of scope; a higher quote is not, by itself, evidence of better coverage.
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The closeout should leave your team with enough information to understand what was tested, what was found, and what to do next. Ask for a redacted sample report early, then compare the proposal’s promised output with what the sample demonstrates.
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Check for reproducible, bounded findings
A useful finding should identify the affected component and give evidence that lets your team understand the conditions under which the issue occurred. It should also state relevant limitations. Without scope and conditions, a finding can be hard to reproduce or interpret; without limitations, readers may mistake a partial test for a claim about the entire system.
Require severity to connect to business impact
Ask how the provider will justify severity and explain the business impact. A rating without its rationale gives decision-makers little basis for prioritizing work. The report should distinguish the demonstrated result from any broader concern or potential consequence the evidence does not establish.
Agree on remediation and retesting
The engagement should include prioritized remediation guidance and a clear path to retest. Confirm whether the provider will help your team interpret findings, whether retesting is included or separately scoped, and what evidence will be supplied to show whether a fix addressed the reported issue. Keep these terms explicit in the proposal and contract so “follow-up” does not mean different things to the buyer and provider.
Understand what a complete assessment lifecycle entails
NIST’s Risk Management Framework describes assessment as determining whether controls are correctly implemented, operate as intended, and meet security and privacy requirements. Its assessment outcomes include selecting an assessment team, approving an assessment plan, producing a report, taking remediation actions, and updating plans. The NIST RMF Assess Step is a useful reference for checking that a proposed engagement has a defined plan and a meaningful closeout.
- Agree on scope and authorization. Resolve the system boundaries, threat model, permitted activities, safety controls, and contacts before work begins.
- Approve the assessment plan. Make sure the plan connects architecture and business risks to test cases, methods, expected evidence, and known limits.
- Conduct the authorized assessment. The provider works within the agreed boundaries and follows the specified stop and escalation conditions.
- Review findings and report. The team receives evidence, affected components, severity rationale, business impact, and coverage limitations in an agreed format.
- Remediate and retest. Prioritize fixes, agree how they will be verified, and update relevant plans based on what the assessment established.
Red flags that warrant a pause
- One-size-fits-all testing: The provider offers the same prompt-focused demonstration regardless of whether your system uses retrieval, tools, agents, or sensitive business workflows.
- Vague scope: The proposal does not identify included systems, integrations, data, or exclusions.
- Unclear authorization: The provider will not document boundaries, approvals, prohibited actions, or stop conditions.
- Unexplained automation: The provider presents tools or volume of tests as a substitute for explaining the method, human review, and coverage.
- Framework name-dropping: The proposal cites a standard but does not say which requirements apply, how findings map to it, or what remains outside scope.
- Thin reporting: The provider cannot show how findings will include evidence, limitations, business impact, and actionable remediation.
- Price without deliverable detail: You cannot determine what testing, reporting, support, or retesting the quoted cost buys.
- Unexamined conflicts: The provider does not answer reasonable questions about who performs the assessment, quality review, or product and implementation relationships.
A concern does not always mean a provider must be eliminated; it may be resolvable with a revised scope or contract. Do not proceed, however, while authorization, safety, or the meaning of the promised deliverables remains unclear.
Make the final selection based on fit and evidence
Score proposals against the same criteria, using your business priorities to decide which deserve the most weight. A simple comparison can keep the discussion focused:
| Criterion | What a strong proposal explains | What to verify |
|---|---|---|
| System fit | How scope and tests reflect your architecture, connected systems, data, and workflows | In-scope and out-of-scope components, assumptions, and exclusions |
| Threat model and method | Realistic abuse cases, human and automated testing, and the reasoning behind test choices | Coverage beyond prompt-only tests and stated limitations |
| Authorization and safety | Written boundaries, approvals, accounts, prohibited actions, escalation, and stop conditions | Who approves work and how the provider handles safety and data |
| Framework use | Relevant mapping to agreed requirements, with versions and applicability explained | What the mapping proves—and what it does not |
| Team and independence | Named delivery roles, relevant experience, review process, and disclosure of potential conflicts | Who will actually do and review the work |
| Evidence and report | Reproducible findings, conditions, limitations, severity rationale, and business impact | A redacted sample and the promised final deliverables |
| Remediation and retesting | Prioritized fixes and an agreed follow-up path | What support or retesting is included and how results will be verified |
| Total cost | Price tied to defined scope, deliverables, and follow-up | Assumptions or changes that may affect the total engagement cost |
Use the table to structure discussion, not to create a false sense of precision. A provider that earns a favorable comparison on one dimension may still be a poor fit if it cannot work safely within your authorization or cannot address the system components that matter most. Before awarding the work, resolve open assumptions and ensure the selected proposal, rules of engagement, and contract describe the same scope and deliverables.
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When to seek a shortlist—and what to verify
A responsible named-provider shortlist depends on details such as your geography, sector and regulatory context, AI architecture, deployment model, risk tolerance, and budget. Without those details, a general recommendation could imply a fit that has not been established. Use the criteria here to develop a shortlist for your circumstances, then verify provider qualifications, availability, contract terms, and framework versions at the time you purchase.
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