Cyber Security Services- Securing Fortune 100 companies since 2014
Penetration Testing

AI & LLM Penetration Testing

AI features change how an application can be attacked. A chatbot, copilot or AI agent can be talked into ignoring its instructions, leaking data from the documents it can read, or taking actions it should never take. Our AI penetration testing attacks your AI applications the way real adversaries do, following the OWASP Top 10 for LLM Applications and MITRE ATLAS, and tests the application, APIs and integrations around the model too. It complements our AI security services and is part of our penetration testing services.

What we test

Prompt injection and jailbreaks
  • Direct prompt injection and jailbreaks that bypass your system prompt and guardrails
  • Indirect prompt injection hidden in documents, emails, web pages or tickets the AI reads
  • System prompt leakage and exposure of hidden instructions or secrets
  • Retrieval-augmented generation (RAG) that returns documents a user should not see
  • Cross-user and cross-tenant data exposure through conversation history, memory or embeddings
  • Sensitive information disclosure: personal data, credentials and business data in responses
  • Excessive agency: agents that can send email, change records, run code or call APIs beyond what the task needs
  • Abuse of tools and connectors, including Model Context Protocol (MCP) servers and plugins
  • Authorization of actions taken on a user’s behalf
  • Improper output handling: model output that becomes cross-site scripting, SQL injection or server-side request forgery downstream
  • Web application and API security of the AI feature itself
  • Model and API key exposure, rate limiting and unbounded consumption that runs up your AI bill
  • Supply chain risks in third-party models, datasets and AI libraries

How Our AI & LLM Penetration Testing Works

Scoping & Threat Modeling

We map your AI application: the model and provider, system prompts, data sources, tools and integrations, user roles, and what a successful attack would look like for your business.

Penetration testing scoping and rules of engagement

Automated & Manual Adversarial Testing

We combine curated attack libraries with hands-on testing by our penetration testers, because the most damaging AI attacks are creative and context-specific.

Penetration testing reconnaissance phase

Application & Integration Testing

We test the APIs, authentication, data retrieval and downstream systems the AI touches, where an AI weakness becomes a real breach.

Penetration testing exploitation phase

Reporting

You receive an executive summary and a technical report mapping every finding to the OWASP Top 10 for LLM Applications and MITRE ATLAS, with example prompts, impact and specific fixes.

Penetration test reporting icon

Remediation Support & Retesting

We help your team strengthen prompts, guardrails, permissions and output handling, then retest to confirm the fixes hold.

Penetration Testing

Test Your AI Before Attackers Do

Schedule a scoping call to plan penetration testing for your chatbot, copilot, RAG application or AI agents.

Get a Fixed-Price Penetration Test Quote

Tell us what you need tested and we will send a fixed-price quote within one business day. Prefer to talk? Book a scoping call.

Frequently Asked Questions

What is AI penetration testing?

AI penetration testing is a security assessment of applications that use large language models or other AI, such as chatbots, copilots, retrieval-augmented generation (RAG) apps and AI agents. Testers try to make the AI ignore its instructions, leak data, misuse its tools or harm downstream systems, and report how to fix what they find.

A web application test looks for flaws in code and access control. AI applications add new attack surfaces in natural language: prompt injection, data leakage through retrieval, and agents with too much authority. We test both, because AI weaknesses usually become serious through the application and integrations around the model.

The OWASP Top 10 for LLM Applications and MITRE ATLAS for adversarial techniques, with findings that also support AI governance programs built on the NIST AI Risk Management Framework and ISO/IEC 42001.

Yes. Agents that can call tools, send messages or change data are one of the highest-risk areas, and we test what an attacker can make them do, including through Model Context Protocol (MCP) servers and plugins.

For commercial AI assistants, the most valuable work is testing how they are configured in your environment, such as what data Copilot can reach through Microsoft 365 permissions and whether oversharing exposes sensitive files. We scope that with you, alongside our AI security assessments.

Pricing depends on the number of AI features, models, data sources and integrations in scope. We provide a fixed quote after a free scoping call.

Reviewed by Matt Santill, CISSP, founder of Cyber Security Services and an original contributor to the NIST Cybersecurity Framework. Last updated .