How to Choose an AI Security Testing Vendor

You’ve decided to get your AI tested. Good. Now you need to pick someone to do it. The AI security testing market is growing fast, and not everyone who claims to test AI actually knows how. Here’s what to look for — and what should make you walk away.

Ask About Their Methodology

The first question to ask any vendor is: what framework do you test against? The answer should include the OWASP Top 10 for LLM Applications at a minimum. If they don’t mention OWASP, they’re probably not up to date on the current threat landscape for AI.

Next, ask whether they do manual testing or rely solely on automated scanning tools. This matters more for AI than for traditional pen testing. AI vulnerabilities — prompt injection, jailbreaks, data leakage through conversational context — require creative, adversarial thinking that automated tools cannot replicate. The best approach is a combination: automated tools for baseline coverage, followed by extensive manual testing by experienced AI security researchers.

If a vendor tells you their “AI security scan” takes two days and runs automatically, you’re getting an automated scan, not a penetration test. Automated tools are a starting point, not a substitute for human expertise.

Ask About Their AI Experience

This is the most important differentiator. Have they actually tested LLM-based applications before? Do they understand how prompt injection works across different model architectures? Can they test RAG (Retrieval-Augmented Generation) pipelines? Do they know how to evaluate AI agent frameworks where the AI can take autonomous actions?

A traditional penetration testing firm that added “AI” to their website last month is not the same as a team that has been doing AI security research and testing at scale. Ask for specific examples of AI systems they’ve tested. Ask what types of vulnerabilities they typically find. If the answers are vague, keep looking.

Ask to See a Sample Report

The report is the deliverable. It’s what you’re paying for. A good AI penetration test report should include a clear executive summary that a non-technical stakeholder can understand, detailed findings with severity ratings based on business impact, proof-of-concept exploits that demonstrate each vulnerability, specific and actionable remediation steps your development team can implement, and mapping to recognized frameworks like OWASP Top 10 for LLMs.

If a vendor can’t show you a redacted sample report, that’s a red flag. Either they haven’t done enough engagements to have one, or their reports aren’t good enough to show. Both are reasons to look elsewhere.

Ask About Pricing and Timeline

Expect to pay $15,000 to $50,000 for a thorough AI penetration test, depending on the scope and complexity of the AI system being tested. A simple chatbot will be on the lower end. A multi-agent system with database access, API integrations, and autonomous action capabilities will be on the higher end.

Be wary of quotes under $10,000 — that’s almost certainly an automated-only assessment that won’t catch the vulnerabilities that matter most. And be wary of quotes over $50,000 from large consulting firms — you’re often paying for the brand name and overhead, not better testing.

Timeline should be 2 to 3 weeks for most engagements. If someone quotes 6 to 8 weeks, you’re likely dealing with a large firm that has scheduling overhead and layers of project management between you and the person actually doing the testing.

Ask Who Does the Actual Testing

This might be the most overlooked question. At large security firms, the person who sells you the engagement is rarely the person who performs the testing. You might get a junior analyst who is still learning AI security, while the senior expert who impressed you in the sales call moves on to the next deal.

At boutique firms that specialize in AI security, you typically get the senior person doing the actual work. Ask directly: who will be testing my system? What is their background in AI security? Will the same person who tests also write the report? The answers will tell you a lot about what you’re actually buying.