AI Penetration Testing and Red Teaming

Comprehensive Security for AI-Enabled Systems

In an era where Artificial Intelligence (AI) and Large Language Models (LLMs) are increasingly integrated into critical business operations, traditional security testing falls short. Standard "AI red teaming" often narrowly focuses on provoking undesirable outputs from the model itself. Arcanum’s AI Penetration Testing Service redefines AI security assessments by adopting a holistic, ecosystem-wide approach. We scrutinize every layer of your AI-enabled applications, from user inputs and data pipelines to the surrounding infrastructure and downstream business workflows, identifying vulnerabilities that simplistic model testing overlooks.

Why Choose Arcanum?

Experience the Difference

Arcanum operates at the forefront of AI security research and practice. Our edge comes from:

Holistic Coverage

Evaluate your entire AI ecosystem, not just isolated model behavior.

Real-World Attack Simulation

Uncover systemic faults attackers will chain together, revealing risks missed by basic testing.

Cutting-Edge Expertise

Leverage our deep research, proprietary taxonomy, and experience with the latest AI technologies.

Actionable Insights

Receive clear, prioritized findings with practical remediation steps tailored to your environment.

Build Trust & Ensure Compliance

Fortify your AI systems to prevent data breaches, maintain regulatory compliance, avoid reputational damage, and build user confidence.

Our Approach

Beyond Traditional Red Teaming

Malicious actors don't just target the AI model in isolation; they exploit the entire interconnected system. Our methodology replicates this full attack kill-chain, assessing how AI integrates with your business and simulating sophisticated attacks that target real-world vulnerabilities across the entire stack – APIs, plugins, data stores, users, and connected systems. We provide assurance far beyond basic "jailbreak" exercises.

Our Seven-Pillar Assessment Methodology

System Input Identification

Thoroughly map all entry points—user interfaces (UIs), APIs, file uploads, tool calls, third-party integrations, and implicit channels (e.g., agent-to-agent communications, micro-services)—to understand how data reaches the model and identify potential injection vectors.

Ecosystem Attack Simulation

Probe the surrounding infrastructure and dependencies—orchestration platforms, model-hosting environments, micro-services, vector databases, metadata stores, logging pipelines, third-party APIs, and auxiliary services—assessing access controls and identifying systemic weaknesses.

Model Security Assessment

Directly assess the AI model itself for vulnerabilities beyond just undesirable content. This includes jailbreaks, policy/safety-filter bypasses, analyzing model versioning, parameter configurations, rate limits, gradient exploits, fine-tune extraction, data poisoning risks, model inversion attempts, and bias amplification.

Prompt Engineering Exploitation

Leverage advanced techniques to test how the AI interprets and executes instructions. This includes logic bombs, context window stuffing, hidden-channel abuse, autonomous agent prompt poisoning, and bypassing designed guardrails through carefully crafted inputs, utilizing our custom Arcanum Prompt Injection Taxonomy.

Data Security and Integrity Analysis

Evaluate the security of data pipelines, training/embedding sets, Retrieval-Augmented Generation (RAG) sources, and data processing.

Application Security Testing

Assess the security of the software application housing or interacting with the AI model. Identify traditional vulnerabilities (e.g., SSRF, XSS, command execution, IDOR in chat UIs, OWASP Top 10) amplified by the AI context, function-calling abuse, insecure output handling, and more.

Pivoting & Lateral Movement

Simulate how real-world attackers chain vulnerabilities and leverage initial footholds (e.g., successful prompt injection) to gain deeper access, escalate privileges, move laterally to adjacent SaaS, cloud, or on-prem assets, and impact other parts of the system or network, demonstrating real business impact (e.g., sensitive data theft, production code commits).

Deep Expertise & Cutting-Edge Techniques

If your AI features touch sensitive data, customer trust, or revenue-critical workflows, Arcanum's AI Penetration Testing Service provides the essential assurance layer you need before and after launch.

Enterprise-Grade Experience

We have hands-on experience assessing complex, enterprise-grade implementations where LLMs and custom AI models are deeply integrated with critical business systems like ERP and CRM, across diverse industries.

Research-Driven Custom Taxonomy

Developed from analyzing hundreds of papers, lectures, and cases studies in both the security, academic AI, and AI jailbreaking scenes.

Our proprietary Prompt Injection Taxonomy covers the latest and most sophisticated attack vectors, with over 60 distinct Evasion Techniques & Classifier Bypass patterns including:

  • Variable Expansion Smuggling
  • ASCII/Unicode Over-Encoding & Manipulation
  • Invisible Unicode Manipulation
  • Chained Agents Exploitation ("Russian Doll Method")
  • Link Smuggling & Embedding
  • JavaScript Payloads ("Time-Bombs") targeting users or systems
  • Plus many more...

Future-Focused & Protocol-Aware Testing

Our methodology adapts to the evolving AI landscape. We actively test systems utilizing emerging integration standards and architectures like:

  • Model Context Protocol (MCP) integrations
  • Agent-to-Agent (A2A) interactions & Multi-Agent Frameworks
  • Multi-modal AI systems (text, vision, audio)
  • Retrieval-Augmented Generation (RAG) pipelines
  • Fine-tuned and custom-trained models
  • Autonomous systems

Advanced Attack Simulation

We employ techniques often missed by standard scans, including dynamic evasion tactics, cross-model exploits, and mimicking Advanced Persistent Threats (APTs) targeting AI supply chains. All testing is performed against live staging or production-equivalent environments mirroring real user data flows.

Secure Your AI Advantage with Arcanum

Ready to see how your AI stack stands up against real adversaries and fortify your AI deployments against tomorrow’s threats?

If your AI features touch sensitive data, customer trust, or revenue-critical workflows, Arcanum's AI Penetration Testing Service provides the essential assurance layer you need before and after launch.


Contact Arcanum Information Security today to discuss your specific needs and schedule a comprehensive AI security assessment.

Drop us a line

Contact us

Say hello, inquire about a service we offer, or leave some feedback!

info@arcanum-sec.com
Somewhere on the Internet
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.