2-SEC PEN TESTING / AI LLM SECURITY

LLM & AI Penetration Testing: Break Your AI on Your Terms, Not Theirs

Adversarial testing for LLM applications, RAG pipelines and AI agents — prompt injection, model abuse and data leakage, uncovered by certified AI/ML penetration testers before your AI reaches production.

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NCSC CHECK OWASP LLM TOP 10 MITRE ATLAS
The problem

Your AI was built to be talked into things. We're the ones who talk it into things first.

Your AI system trusts its users, its documents and its tools — and a single crafted prompt can turn that trust into data loss, unauthorised actions and regulatory exposure under UK GDPR and the EU AI Act.

Prompt injection defeats guardrails

Filters and system prompts are not security boundaries. Indirect injection through documents, emails and web pages quietly redirects your model to serve the attacker's intent.

RAG pipelines leak what they hold

Retrieval systems index everything you gave them. Without access controls tested end to end, one clever query can surface data no user should ever see.

Agents act with real consequences

When your AI can call APIs, send emails or execute code, a hijacked agent isn't a chat problem — it's a foothold in your business systems.

The AI attack surface, in numbers

AI adoption is outpacing AI security.

The industry is shipping LLM features faster than it's securing them — and the first large-scale studies of AI applications are finding the gaps.

~85%

of security teams admit they've used AI tools without a formal security assessment in place.

Source: Gartner survey reporting
Top 3

Prompt injection is OWASP's #1 risk for LLM applications — and indirect injection through retrieved content is the vector defenders see least.

Source: OWASP Top 10 for LLM Applications
100+

LLM-specific vulnerabilities documented by MITRE ATLAS — real attacker techniques demonstrated against deployed AI systems, not theory.

Source: MITRE ATLAS
Seconds

How quickly leaked chat transcripts, retrieval data and agent actions surface once a model is compromised — with no traditional perimeter to slow an attacker down.

Industry incident patterns

Figures reflect published industry research and frameworks at time of writing; sources cited per card. We're happy to walk through the underlying studies on a scoping call.

What is LLM & AI penetration testing?

A full adversarial assault on the model, and everything that trusts it.

LLM and AI penetration testing is a controlled adversarial security assessment in which qualified testers attack AI applications, models, retrieval systems and agents to uncover exploitable weaknesses such as prompt injection, data leakage, tool misuse and broken trust boundaries.

Prompt-Adversarial

Tests direct and indirect prompt injection, jailbreaks and instruction-conflict scenarios designed to override intended behaviour.

Data-Boundary Aware

Challenges RAG pipelines, retrieval permissions and model context to determine whether sensitive or cross-tenant data can be exposed.

Agent-Safe

Tests whether compromised prompts can cause agents to misuse tools, call APIs, execute actions or reach systems beyond their intended permissions.

Evidence-Led

Captures reproducible attack transcripts and proven business impact so teams can harden the model, application and surrounding controls.

AI penetration testing subjects your LLM applications, chatbots, copilots and agents to the same adversarial pressure a real attacker applies — probing prompt injection, jailbreaks, data extraction, tool misuse and the traditional web flaws hiding beneath the model layer.

Our certified AI/ML penetration testers chain model-level findings into business impact: can a customer's document make your assistant exfiltrate another tenant's data? Can a hijacked agent reach internal APIs? Can your fine-tuned model be walked past every guardrail you built?

The result is a report that shows exactly how your AI was attacked, what it revealed, and how to harden it — evidence you can show to boards, regulators, insurers and customers.

As a UK provider working under the NCSC CHECK scheme, our testing is recognised across UK government, financial services and regulated industries — and maps directly to Cyber Essentials Plus, ISO 27001, UK GDPR, DORA and NIS2 obligations faced by UK organisations deploying AI.

AI red teaming vs. model evaluation

Benchmarks tell you how your model performs on average. Adversarial testing proves how it behaves when someone is actively trying to break it — the scenario regulators, customers and your board actually care about.

The AI attack surface, in numbers

AI adoption is outpacing AI security.

The industry is shipping LLM features faster than it's securing them — and the first large-scale studies of AI applications are finding the gaps.

~85%

of security teams admit they've used AI tools without a formal security assessment in place.

Source: Gartner survey reporting
Top 3

Prompt injection is OWASP's #1 risk for LLM applications — and indirect injection through retrieved content is the vector defenders see least.

Source: OWASP Top 10 for LLM Applications
100+

LLM-specific vulnerabilities documented by MITRE ATLAS — real attacker techniques demonstrated against deployed AI systems, not theory.

Source: MITRE ATLAS
Seconds

How quickly leaked chat transcripts, retrieval data and agent actions surface once a model is compromised — with no traditional perimeter to slow an attacker down.

Industry incident patterns

Figures reflect published industry research and frameworks at time of writing; sources cited per card. We're happy to walk through the underlying studies on a scoping call.

Why 2|SEC

Model-layer flaws don't show up on a scanner.

01

AI-first scoping

We scope around how your AI is actually used — the prompts, the data it can reach and the tools it can invoke — not a generic chatbot checklist.

02

We attack the whole chain

The model is rarely the weak point on its own. We test the retrieval layer, the plugins, the identity boundaries and the app code around it — because that's where your AI actually breaks.

03

Threat-modelled, not checkboxed

Every engagement is mapped to the OWASP LLM Top 10 and MITRE ATLAS, then pushed past them — attacker chains specific to your prompts, data and tools.

04

Agents tested with live fire

We exercise tool calls, plugin permissions and sandbox escapes against working systems — under agreed rules of engagement, so your agent's real capabilities get tested, not a demo.

05

Guardrails you can defend

Findings come with concrete fixes at the layer that owns them — prompt architecture, retrieval authorisation, output filtering — not a shrug that says "LLMs are probabilistic".

06

Regression testing as models change

Prompt updates, model swaps and new plugins can reopen old holes. We re-run your adversarial baseline monthly, so drift gets caught before attackers find it.

Choose your target

LLM security today. Every other discipline when your AI reaches them.

Every engagement follows the same business-first process — scoped precisely to the systems that matter to your P&L.

How we work

From first injection to a guardrail that holds.

Six phases, from scoping through to ongoing assurance. Every phase is documented, every finding is actionable.

01

Scoping & pre-test

We map your AI attack surface — the model, its prompts, its data sources, its tools and integrations — and agree safe testing boundaries with your team.

02

Testing

Adversarial testing simulates real-world abuse: direct and indirect prompt injection, jailbreaks, RAG data extraction, agent tool misuse and traditional exploitation of the application layer around your model.

03

Reporting

Every finding is written as an attacker chain — the injection vector, what it reached, and the business data or action at the end of it — with the exploit transcript included, severity scored against the OWASP LLM Top 10, and remediation owned by the layer that can actually fix it. Reports land within 5 working days.

04

Remediation

AI fixes fail in the details. We advise on prompt architecture, retrieval-level authorisation, output handling and agent permission boundaries — then work alongside your engineers, by call or on-site, until the guardrails hold.

05

Retesting

We replay the full attack chains, not just the individual findings — because a patched injection is useless if the same prompt still routes through an unpatched tool call.

06

Regression testing for model drift Optional

A model update, a new plugin or a system-prompt tweak can silently reopen a fixed flaw. We re-run your adversarial baseline every month for 12 months and flag any drift before it becomes exposure.

Credentials

The people who broke it in the lab are the people hardening yours.

Penetration Testing

  • CHECK Team Leaders & Specialist Penetration Testers
  • CHECK Team members across engagements
  • Senior, principal-level expertise across all engagements

Governance, Risk & Compliance

  • ISO 27001 Lead Auditors and Implementors
  • PCI DSS and P2PE QSAs
  • Cyber Essentials (CE Plus) Assessors
  • DORA, CAF and NIS2 Experts

Advanced Offensive Security

  • Certified AI/ML Penetration Testers
  • OSWE (Offensive Security Web Expert)
  • eMAPT (Mobile Application Security)

Your AI will be attacked. Choose who does it first.

Fixed-fee, CHECK-certified, scoped around what your AI can actually reach — its prompts, its data, its tools. One call is enough to size it.

Book a scoping call