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    AI Penetration Testing

    Manual security testing of your LLM applications, RAG pipelines, agents and model endpoints by hands-on experts, mapped to the OWASP Top 10 for LLM Applications 2025 and MITRE ATLAS.

    AI features are shipping faster than the controls around them. A chatbot that reads your knowledge base can be talked into reading someone else's. An agent that can send email, query a database or call an internal API can be steered by text hidden in a document it was asked to summarise. A model endpoint without limits is a cost attack waiting to happen. Automated prompt-fuzzing tools produce long lists of refusals bypassed in a sandbox; they do not tell you whether an attacker can reach your customer data through the retrieval layer or execute a tool they should never have had. Our AI penetration tests are performed by hackers, not scripts, and they answer that question with evidence.

    What is AI penetration testing?

    AI penetration testing is a manual, adversarial security assessment of a system that embeds a large language model or another machine-learning model: the application around it, the prompts and guardrails, the retrieval pipeline and vector store, the tools and agents it can call, the model endpoint itself and the data flows between them. We test it as attackers do: direct and indirect prompt injection, jailbreaks and guardrail bypass, system prompt extraction, data exfiltration through retrieval and memory, cross-tenant leakage in shared vector stores, excessive agency through tool and MCP server abuse, improper handling of model output by downstream code, supply chain weaknesses in models and plugins, and unbounded consumption that turns your token bill into a denial-of-wallet. Findings are mapped to the OWASP Top 10 for LLM Applications 2025 and to MITRE ATLAS techniques, and reported in the terms your AI and platform engineers use.

    Key Capabilities

    Prompt Injection and Guardrail Bypass

    Direct jailbreaks and indirect injection through documents, web pages, emails and tool results, plus system prompt leakage and policy bypass (LLM01, LLM07).

    RAG, Retrieval and Data Exfiltration

    Vector store access control, embedding inversion and poisoning, cross-tenant leakage, over-broad retrieval scopes and sensitive information disclosure through the context window (LLM02, LLM08).

    Agents, Tool Calling and MCP Servers

    Excessive agency: which tools an injected instruction can trigger, with which permissions, against which systems, and whether a human approval step can be skipped (LLM06).

    Output Handling and Downstream Code

    Model output rendered as HTML, executed as code or SQL, or passed to shell and API calls without validation, turning a text model into an injection vector (LLM05).

    Supply Chain and Model Integrity

    Third-party models, fine-tuning datasets, adapters and plugins, model file formats, training and retrieval data poisoning, and the provenance of what you deploy (LLM03, LLM04).

    Abuse, Cost and Unbounded Consumption

    Rate limits, token budgets, recursive agent loops, model extraction attempts and denial-of-wallet scenarios against your inference spend (LLM10).

    Who needs AI penetration testing?

    Organisations deploying customer-facing or internal LLM assistants over company data; product teams shipping agents that can take actions in email, CRM, ticketing or infrastructure; SaaS vendors embedding AI features in multi-tenant platforms; financial institutions and critical-infrastructure operators whose AI systems fall under DORA and NIS2 as ICT systems; and providers or deployers of high-risk AI systems preparing for the obligations of the EU AI Act (Regulation (EU) 2024/1689), including the accuracy, resilience and cybersecurity requirements of Article 15. If a model can read your data or act on your systems, it is part of your attack surface.

    How an AI Penetration Test Works

    01

    Scoping and Threat Modelling

    We map the system: models, prompts, retrieval sources, tools, agents, tenants and data classes, agree the attacker positions and define what a critical finding means for this application.

    02

    Application and API Baseline

    The surrounding web application and APIs are tested first, because authentication, authorisation and session flaws undermine every AI control above them.

    03

    Prompt Injection and Guardrail Testing

    Manual adversarial prompting and indirect injection through every untrusted input the model reads, with adversarial corpora for coverage and a human tester for creativity.

    04

    Retrieval, Memory and Tenant Isolation

    Vector store and retrieval scopes, conversation memory, document permissions and cross-tenant boundaries are attacked for leakage and poisoning.

    05

    Agents, Tools and MCP Servers

    Every tool and MCP server the model can call is enumerated and abused from an injected position to measure the real blast radius of excessive agency.

    06

    Report, Debrief and Retest

    Findings mapped to the OWASP LLM Top 10 2025, MITRE ATLAS and your governance framework, a debrief with your AI and platform teams, and a retest after fixes.

    How We Work

    Manual adversarial testing by OSCP-certified testers, led by Michael van Mameren, who treat the model as one component of an application and attack the whole system: web and API layer, prompts and guardrails, retrieval, tools and agents, and the model endpoint. We use adversarial prompt corpora and automated fuzzing for coverage, but every finding is confirmed by hand, chained to real impact and reproduced with evidence. We do not claim that an automated scanner can secure an LLM application, because it cannot. Rules of engagement cover model abuse, cost ceilings and data handling before the first prompt is sent, critical findings are escalated the same day, and the report maps each finding to the OWASP Top 10 for LLM Applications 2025, MITRE ATLAS and, where you need it, to NIST AI RMF, ISO/IEC 42001 or the EU AI Act.

    What you receive

    Written scope with system map, attacker positions, cost ceilings and data-handling rules
    Findings with severity, evidence, reproduction prompts and prioritised remediation, mapped to the OWASP LLM Top 10 2025 and MITRE ATLAS
    Attack narratives from injected input to data access or tool execution, with the blast radius quantified
    Guardrail, retrieval and tenant-isolation assessment with concrete hardening steps
    Governance mapping to NIST AI RMF, ISO/IEC 42001 and EU AI Act Article 15 where applicable
    Retest of remediated findings with a dated verification appendix

    AI Penetration Testing FAQ

    The questions AI product owners, CISOs and compliance leads ask us before commissioning an AI security assessment, answered straight.

    What is AI penetration testing?

    AI penetration testing is a manual, adversarial security assessment of an application built on a large language model or other machine-learning model, covering the model endpoint, prompts and guardrails, retrieval pipelines, agents and tools, and the surrounding application. It tests for prompt injection, data exfiltration, excessive agency, improper output handling, supply chain weaknesses and abuse, and reports exploitable findings with evidence. It differs from a model evaluation or benchmark because it tests what an attacker can do to your deployment, not how the model scores in isolation.

    What is the OWASP Top 10 for LLM Applications 2025?

    It is the current OWASP list of the most critical risks in LLM applications: prompt injection, sensitive information disclosure, supply chain, data and model poisoning, improper output handling, excessive agency, system prompt leakage, vector and embedding weaknesses, misinformation and unbounded consumption. We use it as the coverage baseline for every AI penetration test, together with MITRE ATLAS, which catalogues real adversary techniques against machine-learning systems, so you can show precisely which risks were tested and with what result.

    Do you test agents, tool calling and MCP servers?

    Yes, and this is where the highest-impact findings now sit. We enumerate every tool and Model Context Protocol server the model can call, test what an injected instruction can make it do, with which permissions and against which systems, and whether human-in-the-loop approvals can be skipped or exhausted. A chatbot that leaks its system prompt is a finding; an agent that can be steered into sending email or changing a record is an incident.

    What is prompt injection and can it be fully prevented?

    Prompt injection is the manipulation of a model through untrusted text, either directly by the user or indirectly through content the model reads, such as documents, web pages or tool results. It cannot be fully prevented at the model layer with current technology, so a secure design limits what a compromised model can reach: least-privilege tools, scoped retrieval, output validation and approval steps for consequential actions. Our test measures how well those boundaries hold, not whether a clever prompt exists.

    How does AI penetration testing relate to the EU AI Act, DORA and NIS2?

    The EU AI Act (Regulation (EU) 2024/1689) requires high-risk AI systems to achieve an appropriate level of accuracy, resilience and cybersecurity under Article 15, with the main high-risk obligations phasing in during 2026 and 2027, and governance frameworks such as NIST AI RMF and ISO/IEC 42001 call for testing and risk treatment of AI systems. DORA and NIS2 treat AI systems as ICT systems and require their security to be tested like any other. An AI penetration test produces the evidence these frameworks ask for, mapped per finding.

    Can an automated AI security scanner do this?

    No. Automated red-teaming tools are useful for coverage and we use them for that, but they generate refusals and jailbreaks in isolation. They do not chain an injection into a retrieval scope to reach another tenant's documents, do not reason about your business logic and do not know which tool call would matter. Every finding we report has been confirmed manually, reproduced and tied to a concrete impact in your system.

    How much does an AI penetration test cost?

    Every test is quoted on scope; there is no fixed price list. The drivers are the number of models and applications, the retrieval sources and tenants, the number and power of the tools and agents, whether the surrounding application and APIs are in scope, the cost ceiling for inference during testing and whether a retest is included. After a scoping call you receive a written proposal within a few working days with the day count and the named lead tester.

    Ready to test your AI systems?

    Hands-on adversarial testing, named certified testers and a report your AI engineers, CISO and compliance team can all act on.