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LLM APPLICATION PENETRATION TESTING

LLM application penetration testing: check your AI assistant cannot be hijacked

Testing of LLM-based applications to the OWASP Top 10 for LLM. Prompt injection, data disclosure, excessive agent permissions and the security of tool integrations.

Testing to the OWASP Top 10 for LLMDirect and indirect prompt injectionAgent permissions and tool integrationsData leakage from context and RAG

WHY IT MATTERS

The model does not tell instructions from data, and you gave it access

LLM-based applications connect the model to your data, tools and actions. The problem is that the model treats the content it processes as a potential instruction. Text from a document, an email or a web page can take over the assistant.

One case from our tests: in a RAG application, a user-uploaded document contained a hidden instruction telling the assistant to reveal another user’s context. That is indirect prompt injection, a class of attack a traditional app test does not cover at all.

WHAT WE CHECK

The full OWASP Top 10 for LLM

01
Prompt injection
Direct and indirect: hijacking model behavior through input and RAG content.
02
Data disclosure
Leakage of data from context, the system prompt and other users.
03
Output handling
Unsafe use of the model’s response, e.g. code or query execution.
04
Agent permissions
Excessive access to tools and actions the agent can invoke without control.
05
Integrations and plugins
Security of tool calls, APIs and external data sources.
06
Abuse and cost
Resource exhaustion, limit bypass and manipulation of model cost.

We tailor scope to the architecture: plain chat, RAG or an agent with tool access.

OUR APPROACH

We attack not just the model, but the whole application around it

LLM application security is not just the model itself. What matters is the data and tools it can access, how input is filtered and what the app does with the response. We test that whole chain, not just individual prompts.

We combine LLM-specific techniques with a classic test of the app and API around the model. It is exactly at the seam between the model and the rest of the system that the worst vulnerabilities arise, for example an agent that performs a dangerous action on an instruction hidden in data.

COMPLIANCE

AI security is entering regulation

AI deployments fall under growing security and risk-management requirements, including the AI Act.

AI Act
Risk-management requirements for AI systems placed on the EU market.
DORA / NIS2
Testing AI components as part of ICT risk management.
ISO 27001
Evidence that controls work (A.8) for apps processing data.

STANDARDS & CERTIFICATIONS

We work to recognized methodologies, not gut feeling

Every project is run by certified pentesters and based on public standards. That makes the result repeatable, auditable and comparable across vendors.

Team certifications
OSCPOSCPOffSec
OSEPOSEPOffSec
OSWEOSWEOffSec
OSEDOSEDOffSec
OSWAOSWAOffSec
OSWPOSWPOffSec
BSCPBSCPPortSwigger
CPTSCPTSHack The Box
CBBHCBBHHack The Box
CWEECWEEHack The Box
CRTOCRTOZero-Point Security
CREST CRTCREST CRTCREST
CREST CPSACREST CPSACREST
ISO 27001 LAISO 27001 LAISO/IEC
Azure Security EngineerAzure Security EngineerMicrosoft
Security Operations AnalystSecurity Operations AnalystMicrosoft
Security AdministratorSecurity AdministratorMicrosoft
OSCPOSCPOffSec
OSEPOSEPOffSec
OSWEOSWEOffSec
OSEDOSEDOffSec
OSWAOSWAOffSec
OSWPOSWPOffSec
BSCPBSCPPortSwigger
CPTSCPTSHack The Box
CBBHCBBHHack The Box
CWEECWEEHack The Box
CRTOCRTOZero-Point Security
CREST CRTCREST CRTCREST
CREST CPSACREST CPSACREST
ISO 27001 LAISO 27001 LAISO/IEC
Azure Security EngineerAzure Security EngineerMicrosoft
Security Operations AnalystSecurity Operations AnalystMicrosoft
Security AdministratorSecurity AdministratorMicrosoft
Methodologies
OWASP Top 10 for LLMMITRE ATLASPTES
Verification standards
OWASP ASVS 5.0.0
Scope
Prompt injectionAgent securityTool integrations

We share the full list of certifications and standards on request, together with a sample test scope.

HOW WE DO IT

A repeatable process for AI applications

01
Scoping
We define the architecture, model, data sources and available tools.
02
Mapping
We map the data flow: input, context, RAG, agent actions.
03
LLM testing
We check prompt injection, data leakage and permission abuse.
04
App and API
We test classic vulnerabilities in the layer around the model.
05
Report and retest
We deliver a prioritized report and, after fixes, confirm the issues are gone.

EVIDENCE

Numbers behind every promise

Every test is run by certified pentesters, and we document the result with reproduction steps, evidence and a verified remediation path. Proof, not a promise.

500+
security tests and audits completed
5.0
average score from 10 verified Clutch reviews
20+
offensive certifications across the team
01
Certified team
20+ offensive certifications across the team (OSCP, OSEP, OSWE, CREST). Tests are run by our people, not anonymous subcontractors.
02
Manual testing
We work by hand to PTES and OWASP, chaining seemingly small flaws into a real, proven attack path.
03
Evidence, not a promise
Every finding comes with reproduction steps and a working proof. A report that holds up in front of an auditor.
04
Retest included
After fixes are deployed we confirm in writing that the gaps are closed. We do not vanish once the PDF is sent.

KNOWLEDGE

LLM application security testing in practice

Why apps built on a language model need a new approach

An application built on a language model takes user text as an instruction, so the line between data and command blurs. We test it to the OWASP Top 10 for LLMs, covering both the model itself and its integrations with data and tools.

A classic scanner is not enough here, because the risk does not sit in a single request but in how the model interprets content. So we work through scenarios in which an attacker tries to take control of the application behavior.

Prompt injection and data leakage

The most important class of risk is prompt injection: direct, where the user openly manipulates the instruction, and indirect, where a malicious instruction hides in the data the model retrieves. We check whether this can bypass rules or extract the hidden system prompt.

We also test data leakage: whether the model exposes content the user should not access, including other users data or knowledge base information. This is a common result of over-trusting whatever the model receives in its context.

Excessive agency in agents and integrations

When the model can call tools, send queries or trigger actions, the risk of excessive agency appears. We check whether the application can be forced into an operation the user should not be able to perform, and whether the model output is handled safely.

Unsafe handling of the model response, for example executing it as code or a query, can turn a vulnerability into a full takeover. That is why we look not only at the model but at the entire chain around it.

What you get and when to test

The report describes every attack scenario with evidence and a concrete business impact, along with recommendations covering the system prompt, validation, least privilege and data filtering. We translate the risk into the language of decisions, not just technique.

An LLM application is worth testing before the feature reaches users and after every change to the model, system prompt or integrations. Each of these can open a new path to abuse.

FAQ

Common questions

Do you test the model or the application?

The whole application around the model: input, context, RAG, tools and response handling. That is where the worst vulnerabilities arise.

Do you cover agents and RAG?

Yes. Agents with tool access and RAG systems have specific attack classes, such as indirect prompt injection, which we include in scope.

Does this replace an API test?

No. An LLM test complements a classic app and API test with the model-specific layer. Combining both gives the best result.

Is the retest included?

Yes. After fixes ship we re-test the listed flaws and confirm they are gone.

RELATED

Related reading

CASE STUDIES

Case studies in this area

REFERENCES

“The project was delivered professionally and on time, with a strong grasp of both technology and business. We were impressed by their cybersecurity expertise and partnership approach.”
M
Mateusz Widenka
Head of Delivery, Order Group
Clutch★★★★★5.0 · 10 reviewsRead all reviews on Clutch

FIRST STEP

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Tell us what you want tested. Within 24 hours you get a proposed scope and next steps. You talk to a consultant who understands the technical side, not a salesperson.

Get in touch
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Methodology
PTES · OWASP
Team
20+ certifications
Rating
5.0 on Clutch
What you get
A scope proposal matched to your risk
A report with evidence and reproduction steps
Remediation priorities by real impact
A retest after fixes are deployed
Asia, ElementricaKacper, ElementricaGrzesiek, Elementrica
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