AI/LLM Penetration Testing

Human-led security testing for AI-enabled applications, LLM workflows, and MCP integrations. We test the way a real attacker would, then show you exactly what we found and how to fix it.

This is testing for the AI features you ship to users, not AI standing in for a tester. Every engagement is run by our own pentesters.

0

pentests delivered

0

vulnerabilities surfaced

0.0 on G2

and Capterra

AI/LLM Penetration Testing

Human-led security testing for AI-enabled applications, LLM workflows, and MCP integrations. We test the way a real attacker would, then show you exactly what we found and how to fix it.

This is testing for the AI features you ship to users, not AI standing in for a tester. Every engagement is run by our own pentesters.

0

pentests delivered

0

vulnerabilities surfaced

0.0 on G2

and Capterra

AI/LLM Penetration Testing

Human-led security testing for AI-enabled applications, LLM workflows, and MCP integrations. We test the way a real attacker would, then show you exactly what we found and how to fix it.

This is testing for the AI features you ship to users, not AI standing in for a tester. Every engagement is run by our own pentesters.

0

pentests delivered

0

vulnerabilities surfaced

0.0 on G2

and Capterra

THE REALITY CHECK

THE REALITY CHECK

AI features moved faster than the testing did

AI features moved faster than the testing did

AI features moved faster than the testing did

Your team shipped an assistant, a copilot, a RAG-backed search box, or an agent that can take actions. It works. That is exactly the problem, because working software still has exploitable paths, and AI features add new ones on top of the app, API, cloud, and auth risks you already had.

Most AI risk is not mystical. A model that can call a tool can be talked into calling it in ways you did not intend. A model with access to a document store can be steered into returning documents the user was never allowed to see. An integration that connects a model to your business systems becomes a new way in. We test for the version of these problems that an attacker can actually reach and abuse.

Your team shipped an assistant, a copilot, a RAG-backed search box, or an agent that can take actions. It works. That is exactly the problem, because working software still has exploitable paths, and AI features add new ones on top of the app, API, cloud, and auth risks you already had.

Most AI risk is not mystical. A model that can call a tool can be talked into calling it in ways you did not intend. A model with access to a document store can be steered into returning documents the user was never allowed to see. An integration that connects a model to your business systems becomes a new way in. We test for the version of these problems that an attacker can actually reach and abuse.

Your team shipped an assistant, a copilot, a RAG-backed search box, or an agent that can take actions. It works. That is exactly the problem, because working software still has exploitable paths, and AI features add new ones on top of the app, API, cloud, and auth risks you already had.

Most AI risk is not mystical. A model that can call a tool can be talked into calling it in ways you did not intend. A model with access to a document store can be steered into returning documents the user was never allowed to see. An integration that connects a model to your business systems becomes a new way in. We test for the version of these problems that an attacker can actually reach and abuse.

What we test

We test AI-enabled systems end to end, including agents, tool-calling, and MCP integrations, when the engagement is scoped and staffed for it. We do not sell autonomous AI-run testing as a product, and no AI performs the assessment on our end. A Red Sentry pentester runs every test on this page.

The model and its prompts

The model and its prompts

  • Prompt injection and indirect prompt injection (instructions smuggled in through user input, documents, web pages, or upstream data)

  • Sensitive data leakage and system prompt exposure

  • Model abuse scenarios (getting the system to do something it should refuse)

The data the model can reach

The data the model can reach

  • RAG and source exposure (retrieving records, files, or context the user should never see)

  • Tenant isolation and authorization gaps in AI-driven workflows

The tools and connectors the model can act through

The tools and connectors the model can act through

  • Unsafe tool or function calling

  • Excessive tool permissions

  • MCP and connector risk, a growing attack surface, covered in detail below

Where AI meets your existing stack

Where AI meets your existing stack

  • Insecure API integrations and insecure output handling (unvalidated model output flowing into your app, browser, or downstream systems)

  • Business logic abuse (chaining an AI weakness with an app, API, or cloud flaw into real impact)

AGENTIC RISK

MCP and tool-calling: an emerging attack surface

MCP (Model Context Protocol) and similar tool-calling architectures connect an LLM to external tools, data sources, files, APIs, commands, and business workflows. That connection is exactly why it matters. It turns model output into something that can act, not just something that talks.

When MCP servers, connectors, or tool-calling are part of your environment, we evaluate whether those integrations are least-privileged, properly authorized, auditable, and resistant to prompt or tool manipulation, including:

Tool-description injection and tool-output or resource-based prompt injection

Malicious or overtrusted MCP servers, and cross-server trust issues

Excessive tool permissions and unsafe tool or function execution

Credential or token exposure

Conversation or context leakage

Authorization gaps between the user, the model, MCP servers, tools, and downstream systems

Unsafe access to files, APIs, commands, or business workflows

Logging, monitoring, approval-flow, and auditability gaps

This work is scoped and staffed to match your architecture — we confirm tester depth before the engagement is scoped.

Why it matters

AI features can expose sensitive data, trigger actions no one approved, bypass controls you thought were enforced, or open a fresh path into the apps, APIs, cloud services, and internal workflows behind them.

The blast radius is not the chatbot. It is everything the chatbot is connected to.

Three ways this shows up in real engagements:

A support assistant that can be steered into returning another customer's records

An agent with a connected tool that can be pushed into an action the user was never authorized to take

Model output that gets trusted downstream and becomes a classic injection into your own app

TESTS COMPARISON

Scanners find patterns. We find the path.

Scanners find patterns. We find the path.

FEATURE

Automated AI scanner

Red Sentry AI/LLM pentest

Prompt injection

Known templates and signatures

Novel payloads, indirect injection through documents and data

Tool and MCP abuse

Not evaluated

Tests what the model can actually trigger and whether it can be abuse

Authorization and
tenant isolation

Not evaluated

Tested against your real roles and data boundaries

Findings

Long list, many false positives

Validated findings with evidence and business impact

Who runs it

Software

Our pentesters, every engagement

Automated AI scanner

Red Sentry AI/LLM pentest

Feature

Automated AI scanner

Prompt injection

Known templates and signatures

Tool and MCP abuse

Not evaluated

Authorization and

tenant isolation

Not evaluated

Findings

Long list, many false positives

Who runs it

Software

HOW WE WORK

How we scope it

Scope depends on your system, not a fixed package. Before testing, we work with you to map:

When MCP, agents, or advanced tool-calling architecture are part of your environment, we match your engagement team to that architecture before the work is scoped.

Model and provider (hosted API, self-hosted, fine-tuned)

Model and provider (hosted API, self-hosted, fine-tuned)

Use case and what the feature is allowed to do

Use case and what the feature is allowed to do

User roles and the auth model

User roles and the auth model

Environments (production, staging) and any testing restrictions

Environments (production, staging) and any testing restrictions

Tenant model (single vs multi-tenant)

Sensitive data in play

Sensitive data in play

MCP servers, connectors, tools, plugins, and actions available to the model

MCP servers, connectors, tools, plugins, and actions available to the model

RAG and data sources the model can reach

RAG and data sources the model can reach

API endpoints in scope

API endpoints in scope

When MCP, agents, or advanced tool-calling architecture are part of your environment, we match your engagement team to that architecture before the work is scoped.

When MCP, agents, or advanced tool-calling architecture are part of your environment, we match your engagement team to that architecture before the work is scoped.

What you get

Validated findings

Every issue is confirmed by a tester, not passed along from a tool.

Evidence and impact

Proof, business risk, and a clear path showing how it could be reached.

Remediation guidance

Clear steps your engineers can use to fix the issue quickly.

Technical report plus executive summary

Depth for fixers and a clear risk picture for decision-makers.

Remediation testing

One retest round is included for final-report findings within 90 days.

The Red Sentry platform

Live findings, remediation tracking, Jira integration, and auditor-ready reporting.

What you get

Validated findings

Every issue is confirmed by a tester, not passed along from a tool.

Evidence and impact

Proof, business risk, and a clear path showing how it could be reached.

Remediation guidance

Clear steps your engineers can use to fix the issue quickly.

Technical report plus executive summary

Depth for fixers and a clear risk picture for decision-makers.

Remediation testing

One retest round is included for final-report findings within 90 days.

The Red Sentry platform

Live findings, remediation tracking, Jira integration, and auditor-ready reporting.

How the engagement runs

Scoping

We map your AI system, integrations, data access, and testing restrictions with your team.

Scoping

We map your AI system, integrations, data access, and testing restrictions with your team.

The test

Our pentesters run the engagement by hand, chaining findings the way an attacker would.

The test

Our pentesters run the engagement by hand, chaining findings the way an attacker would.

The report

You get validated findings, evidence, impact, and remediation guidance, plus live visibility in the platform as we go.

The report

You get validated findings, evidence, impact, and remediation guidance, plus live visibility in the platform as we go.

Remediation testing

After you fix the findings in your final report, we perform one round of remediation testing when requested within 90 days of delivery, unless otherwise defined in the engagement.

Remediation testing

After you fix the findings in your final report, we perform one round of remediation testing when requested within 90 days of delivery, unless otherwise defined in the engagement.

Compliance and AI risk frameworks

Compliance and AI risk frameworks

Our methodology references the OWASP Top 10 for LLM Applications, MITRE ATLAS, and NIST AI RMF. AI/LLM Security Testing can also support SOC 2, ISO 27001, HIPAA, GDPR, and other compliance evidence needs when AI systems are part of the assessed environment.

Frameworks are a reason to test, not a test on their own. We perform the technical testing and give you evidence you can hand to your auditor. We do not certify or attest compliance, and no single test makes you compliant by itself.

Related Services

Test your AI before an attacker does.

Tell us what you are building and we will scope it. Human-led, evidence-backed, and mapped to real impact.

Test your AI before an attacker does.

Tell us what you are building and we will scope it. Human-led, evidence-backed, and mapped to real impact.