AI Penetration Testing Services


Find prompt injection, data leakage, unsafe outputs, insecure agent workflows, and other AI-specific risks before attackers do.

Why Security Teams Choose Outpost24 for AI Penetration Testing

Outpost24 helps organizations uncover weaknesses in LLMs, AI-powered applications, and agentic systems through expert-led adversarial testing.

AI-Specific Risk Coverage

Identify prompt injection, insecure outputs, model misuse, data leakage, and agent manipulation that traditional tools cannot detect. 

Real-World Adversarial Testing

Experienced penetration testers evaluate how your AI systems behave under real-world adversarial conditions using AI-specific methodologies and OSAI+ guidelines. 

Actionable Findings for Faster Remediation 

Get prioritized findings, AI-specific remediation guidance, and audit-ready reporting through a single platform. 

Expert-Led Penetration Testing for AI and LLMs

As organizations embed AI into customer-facing applications, internal workflows, and agentic systems, they create a new AI attack surface that requires dedicated adversarial testing.

Discovery and Scope Mapping

Our experts map your AI environment, including models, prompts, RAG pipelines, agents, APIs, and connected systems. 

Adversarial Testing

Performed by our certified penetration testers, we simulate real-world attacks against prompts, workflows, permissions, integrations, and data access paths. 

Screenshot Chat Managed Services Outpost24

Findings and Remediation

Receive prioritized findings aligned to the OWASP Top 10 for LLMsremediation guidance tailored to AI architectures, and audit-ready reporting. 

certifications Outpost24

Our Experts’ Certifications

  • OffSec’s Experienced Penetration Tester (OSEP)
  • Certified Azure Red Team Professional (CARTP)
  • Certified Information Systems Security Professional (CISSP)
  • The Council for Registered Ethical Security Tester (CREST)
  • Certified Red Team Professional (CRTP)
  • Certified Red Team Operator (CRTO)
  • Certified Red Team Lead (CRTL)
  • eLearnSecurity Certified Professional Penetration Tester (eCPPT)
  • eLearnSecurity Web Application Penetration Tester (eWPT)
  • eLearnSecurity Web Application Penetration Tester eXtreme (eWPTX)
  • Exploit Researcher and Advanced Penetration Tester (GXPN)
  • OSSTMM Professional Security Tester (OPST)
  • Offensive Security Certified Expert (OSCE)
  • OffSec Certified Professional (OSCP)
  • OffSec Web Expert (OSWE)

Compliance Readiness 

Simplifyyour compliance and audit efforts. Outpost24 AI Penetration Testing supports organizations preparing for the EU AI Act and NIST AI RMF. 

Frequently Asked Questions

We test the full AI attack surface, including LLM prompts, guardrails, and system instructions, Retrieval-Augmented Generation (RAG) pipelines, agent workflows and tool use, supporting APIs, interfaces, and integrations, access controls between models and internal systems, sensitive data exposure risks, unsafe outputs and harmful model behavior and the authentication, authorization, and session controls around AI services. 

Yes. Testing before launch helps identify vulnerabilities earlier, when they are typically faster and less costly to fix. It also gives your team more confidence before go-live and helps demonstrate security due diligence from day one. 

Partially. Our web application assessments include testing of AI-integrated functionality within the application scope. However, they do not cover AI-specific risks at a deeper level, including those related to the underlying model and infrastructure. A dedicated AI/LLM pentest is recommended when AI is a core part of the product. If unsure, bring it up at scoping and the team will advise on the right approach.

Want to Know More?

Explore additional resources.

Outpost24 AI Penetration Testing

Comprehensive overview of our AI Pen Testing Services
View Datasheet

Penetration Testing Services

Expert-led penetration testing across web and mobile apps, APIs, networks, and cloud.
Discover Pen Testing Services

63% of organizations have no AI governance policy

AI penetration testing helps uncover risks in access control, data handling, and system behavior across AI systems and LLM integrations.
Read Blog

Get a Quote

Please fill in your information to get in touch with our security experts. All fields are mandatory.

Need Support?

Stay in the Loop with Outpost24

Check our latest research, blogs, and best practices to level-up your cybersecurity program.

View All Posts