AI & LLM
Penetration Testing
Your AI application accepts natural language as input.
That makes every user interaction a potential attack vector.
01 // Why This Matters Now
EU AI Act
Full compliance required by August 2, 2026. High-risk AI systems require mandatory adversarial testing — non-compliance penalties reach €35M or 7% of global turnover.
NIS2 & DORA
AI systems automating critical decisions are increasingly in-scope under NIS2 and DORA. Security testing of AI components is no longer optional in regulated industries.
The Methodology Gap
Traditional pentesting doesn't test whether your RAG pipeline leaks documents or whether an AI agent can be tricked into unauthorised API calls. This gap is active and unaddressed in most organisations.
02 // What I Test
Your architecture determines your attack surface. We establish which layers are in scope during scoping.
Every AI App
Prompt injection, jailbreaking, system prompt extraction, and sensitive data disclosure — present in any LLM-based system.
Knowledge Base / RAG
Indirect prompt injection via retrieved content, cross-tenant knowledge leakage, and knowledge base poisoning.
Tool Access / Agentic
Tool call hijacking, privilege escalation through chained calls, and confused deputy attacks reaching real systems.
Multi-Agent Orchestration
Cross-agent prompt injection, inter-agent auth weaknesses, and trust boundary violations between orchestrator and sub-agents.
Running a self-hosted or fine-tuned model? A fifth layer covering model integrity, training data exposure, and membership inference is available on request.
03 // Indicative Pricing
Exact quote after scoping call. Complexity of the AI architecture — number of attack surfaces, agentic integrations, and tool connections — determines the final price.
40% Portfolio Discount — Building My AI Testing Practice
I am offering a 40% discount on all AI testing engagements to clients who agree to be referenced as an anonymised case study. Your organisation's name is never disclosed — only the industry, AI architecture type, and anonymised findings. This offer is time-limited as my portfolio fills.
- › Automated prompt injection & jailbreak battery
- › System prompt extraction attempts
- › Sensitive information disclosure testing
- › Basic output validation
- › RAG leakage check (if applicable)
- › Written report + debrief call
Ideal for: organisations with a chatbot or RAG assistant that has never been tested
- › Manual attack chain development
- › RAG pipeline attacks & knowledge base poisoning
- › Tool call hijacking & privilege escalation
- › Cross-agent injection (if applicable)
- › EU AI Act / NIS2 / DORA regulatory mapping
- › Retest of critical findings + debrief call
Ideal for: agentic systems, RAG with tool access, regulated sectors requiring documented testing
- › Custom threat modelling workshop
- › Multi-layer attack chain development
- › Goal-based adversarial simulation
- › Multiple AI systems / business units
- › Executive business impact analysis
- › Custom delivery timeline
AI systems change with every model update, new tool integration, and prompt revision. Monthly or quarterly automated retesting with a brief update report gives you an ongoing audit trail for compliance. The most cost-effective way to maintain coverage over time.
All prices indicative. Exact quote after scoping call. Each additional tool integration or agentic pipeline adds independent attack paths and is scoped separately.
Book Free Scoping Call04 // How We Collaborate
We map your AI architecture, identify which attack surfaces apply, and establish the blast radius of a potential compromise.
I fingerprint guardrails, attempt system prompt extraction, and build the attack plan before active testing begins.
Systematic prompt injection, jailbreak, RAG, and tool-call testing — each finding confirmed through multiple reproductions.
Executive summary with regulatory mapping + technical appendix with reproduction steps and remediation guidance. Debrief call included.
Is your AI deployment tested?
Most organisations deploying AI in 2026 have never had their AI systems tested by a security professional. With EU AI Act deadlines approaching, that's a compliance gap that won't stay quiet.