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OFFENSIVE SECURITY / AI, LLM & AGENTS

AI & LLM Security Testing

AI systems are creating a new layer of application risk. Test models, prompts, agents, tools and data flows as part of the modern attack surface.

AI features are increasingly wired into real applications — reading documents, calling internal APIs, querying knowledge bases and taking actions on a user’s behalf. That connectivity is what makes them useful, and it is also what makes them a security surface.

The distinguishing property is that instructions and data arrive through the same channel. A model reading a retrieved document cannot inherently tell the difference between content it should summarise and text written to be followed. Traditional application security models were not designed around that. See Why Are AI & LLM Applications Vulnerable? for a closer look at why.

The AI request path

Risk concentrates where the model stops producing text and starts triggering actions.

  1. USERUserThe person or system making the request
  2. PROMPTPromptSystem instructions, user input and injected context
    Untrusted content enters here
  3. MODELModelThe model and its configured behaviour
  4. AGENTAgentPlanning, autonomy and decisions about what to do next
    Text becomes action here
  5. TOOLSToolsFunctions, APIs and integrations the agent can call
  6. DATADataKnowledge sources, retrieval and records reachable through tools
  7. APPApplicationWhat the surrounding application does with the result

Conceptual view of a typical AI application. Assessment is scoped to the systems you authorize.

// DEFINITION

What is AI / LLM security testing?

AI / LLM security testing is a manual assessment of AI and large-language-model-powered systems for prompt injection, jailbreak resistance, data leakage beyond a requester’s entitlement, system prompt exposure, tool abuse, excessive agency, and agent security in multi-step or autonomous behaviour. TMG Security maps the request path, identifies where untrusted content enters the system, probes instruction handling and boundary enforcement, assesses connected tools, and establishes what a successful influence attempt would actually achieve.

Who needs it? Products shipping AI features, LLM-powered applications, agent and automation platforms, retrieval-augmented generation (RAG) systems built over sensitive data, AI customer support, and internal AI tooling, most often when an AI feature is about to ship and is wired to real data or real actions for the first time.

How TMG Security helps. TMG Security follows a map, trust, probe, tools, impact, report methodology built for AI systems, and delivers findings with reproduction detail, mitigation guidance and a report your team can act on.

// FOCUS AREAS

Focus areas

// CONTEXT

Where AI risk actually concentrates

A model that only returns text has a bounded blast radius. The picture changes once the same model can call a tool, query a database or send a message — the output stops being a suggestion and becomes an action. This is the risk surface covered in Agentic AI Security.

So the practical question is rarely whether a model can be talked into saying something it should not. It is what the surrounding system permits when it does: which tools are reachable, whose data those tools can retrieve, and what happens downstream without a human in the loop.

Not every AI deployment carries meaningful risk. A narrow, read-only feature with no tool access is a very different proposition from an agent with write access to production systems, and assessment should be scoped accordingly.

// HOW IT DIFFERS

How AI / LLM security differs from traditional application security

Traditional application security tests a system with fixed, deterministic logic: the same request produces the same response, and testing focuses on authentication, authorization, session handling and input validation across a known set of code paths. AI and LLM-powered systems introduce a different kind of risk. The same input can produce different outputs depending on context, instructions can arrive embedded in ordinary-looking content rather than through a defined input field, and a model connected to tools can turn a successful prompt injection into a real action rather than just an unwanted response.

This is why AI / LLM testing adds focus areas that traditional application testing does not cover on its own: prompt injection, jailbreak resistance, system prompt exposure, tool abuse, excessive agency and multi-step agent behaviour. Where an AI feature also exposes a conventional web application or API, both forms of testing are relevant and are typically scoped together.

// METHODOLOGY

How we assess AI systems

  1. 01MAPEstablish the request path: inputs, context sources, tools and downstream effects.
  2. 02TRUSTIdentify where untrusted content enters and what it can influence.
  3. 03PROBETest instruction handling, restrictions and boundary enforcement.
  4. 04TOOLSAssess what connected tools permit and how arguments are constrained.
  5. 05IMPACTEstablish what a successful influence attempt would actually achieve.
  6. 06REPORTFindings with reproduction detail and mitigation guidance.
// WHO THIS IS FOR

Organizations this typically applies to.

Products shipping AI featuresLLM-powered applicationsAgent & automation platformsRAG over sensitive dataAI customer supportInternal AI tooling

Testing is scoped per engagement. Nothing here implies industry-specific certification or accreditation.

// WHEN THIS APPLIES

When Does an AI Feature Warrant Assessment?

01SITUATIONAn AI feature is about to shipThe model is wired to real data or real actions for the first time.
02SITUATIONAn agent gained tool accessThe system stopped producing text and started taking actions.
03SITUATIONRAG over sensitive contentRetrieval now reaches documents not everyone should see.
04SITUATIONCustomers are asking about AI riskBuyers have started including AI questions in security review.
// WHAT YOU RECEIVE

A report your team can actually act on.

Exact deliverables and their format are confirmed during scoping.

EXECUTIVE SUMMARY

What was assessed, what was found and what it means, written to be read by people who will not read the technical detail.

TECHNICAL FINDINGS

Each finding described with enough precision for an engineer to locate and understand it.

EVIDENCE

Reproduction detail and supporting evidence, so findings can be verified rather than taken on trust.

RISK CONTEXT

Severity considered against your environment, not only against a generic scoring table.

REMEDIATION GUIDANCE

Practical direction on addressing each finding, including where a change belongs architecturally.

RETEST / VALIDATION

Verification that addressed findings no longer reproduce, within the agreed retest scope.

// PRICING & ENGAGEMENT

How pricing and scope are determined

There is no published fixed price for AI / LLM security testing. Each engagement is scoped and priced individually based on factors such as the number of AI features or models in scope, the complexity of the system, for example a single model versus a multi-agent or tool-integrated system, and the testing depth agreed for the engagement. These factors are discussed during scoping before a quote is provided.

// FREQUENTLY ASKED

Questions we get asked before an engagement.

Explore AI Security Testing

Tell us what your AI feature can read, call and act on. That determines whether assessment is worthwhile and, if it is, what it should cover.