AI Security Testing

What is AI Systems Penetration Testing?

AI systems penetration testing is a specialized security assessment for LLMs, chatbots, and AI-enabled applications that evaluates attack surfaces unique to AI vulnerabilities that traditional penetration testing frameworks do not cover (including model manipulation, training data extraction, and context window abuse). Required for high-risk AI systems under the EU AI Act (Regulation EU 2024/1689), with deadlines shifted to 2 December 2027 (Annex III) and 2 August 2028 (Annex I) under the Digital Omnibus agreement of 7 May 2026.

Focused and context-aware. Penetration testing for AI and machine learning systems such as LLMs, chatbots, and AI functionality within applications. We test prompt injection, data leakage, and the effectiveness of guardrails to uncover abuse and unintended behaviour early.

Request Quote Contact Us

What is the testing scope?

LLM prompt injection testing

Model manipulation and poisoning

AI output validation bypass

Data extraction through AI interfaces

Jailbreaking and guardrail bypass

AI-assisted attack surface analysis

How do we approach AI testing?

Prompt Analysis

We test whether AI systems can be manipulated through prompts, context manipulation, or hidden instructions. This helps identify how users or attackers might steer the model beyond its intended behaviour.

Guardrail Testing

We deliberately attempt to bypass existing safety rules and restrictions. This reveals where guardrails fall short and which risks arise from misuse or unintended behaviour.

Data Leakage

We assess whether sensitive information can be exposed through model responses, prompts, or connected systems. This includes testing for both direct leakage and indirect exposure via integrations.

What does EU AI Act Article 15 require?

High-risk AI systems under Annex III of the EU AI Act must meet cybersecurity requirements. The Digital Omnibus agreement of 7 May 2026 moved the compliance deadline from 2 August 2026 to 2 December 2027 (stand-alone Annex III) and 2 August 2028 (Annex I, embedded in regulated products). A structured AI pentest is the most direct path to documented Article 15 compliance.

What is a high-risk AI system?

Annex III of the EU AI Act includes AI systems used in hiring decisions, credit scoring, biometric identification, critical infrastructure management, and education. If your AI system falls under Annex III, security testing under Article 15 is a legal requirement, not a best practice.

Article 15: what it requires

Article 15 requires high-risk AI systems to be designed and developed to withstand attempts to alter their outputs or behaviour through adversarial inputs. A structured AI penetration test produces documented evidence that your system meets this requirement.

Deadline: 2 December 2027

The Digital Omnibus agreement of 7 May 2026 moved the compliance deadline for stand-alone high-risk AI systems under Annex III from 2 August 2026 to 2 December 2027. AI embedded in regulated products under Annex I (medical devices, machinery, toys) shifts to 2 August 2028. Begin your assessment well before these dates to allow time for remediation and retesting.

Audit evidence for conformity

An AI penetration test produces findings mapped to EU AI Act Article 15 requirements. This gives your compliance team and conformity assessment body concrete, auditable evidence that security obligations are met before the deadline.

How does an AI pentest differ from a classic pentest?

AI security testing and classic application penetration testing overlap in some areas and diverge in others. Understanding the difference helps you scope the right assessment for your situation.

What's the same

Both assess how an application responds to malicious input. Authentication flows, API security, authorization logic, injection attacks, and data exposure risks are tested in both disciplines. If your AI system is embedded in a web application, both test types apply.

What's unique to AI

Prompt injection, context window manipulation, training data extraction, jailbreaking, guardrail bypass, and tool-call abuse are attack vectors that only exist in AI systems. Standard web application testing tools and methodologies do not cover these attack surfaces.

Why you need both

An AI system embedded in a web application inherits the vulnerabilities of both layers. We recommend combining AI security testing with web application or API testing for complete coverage. A single assessment can address both, with a unified evidence package for auditors.

Frequently Asked Questions

We test LLM-based apps, chatbots, AI assistants, ML-driven features, and AI integrations including retrieval-augmented generation (RAG), tool-calling, and multi-agent workflows.

Yes. We assess prompt injection, instruction override, jailbreak attempts, and guardrail bypass paths, including tool-call abuse when applicable. We follow the OWASP LLM Top 10 framework and extend it with context-specific attack chains relevant to your system.

Yes. High-risk AI systems under Annex III of the EU AI Act must comply with Article 15 cybersecurity requirements by 2 December 2027 (stand-alone systems) or 2 August 2028 (AI embedded in regulated products under Annex I), following the Digital Omnibus agreement of 7 May 2026. Our AI penetration test produces findings mapped to Article 15 obligations, giving your compliance team auditable evidence of conformity.

Yes. We test for unintended disclosure of sensitive data via model outputs, memory, retrieval sources, file and tool access, and other AI interfaces.

Absolutely. Many AI risks live in the surrounding application, APIs, authentication, and integrations. We can combine both assessments for a complete view and a single unified evidence package.

Assess your AI security posture

Get a comprehensive view of your AI system vulnerabilities and EU AI Act compliance readiness.