AI Chatbot Penetration Testing

AI chatbots don’t behave like traditional applications—and attackers know it. They exploit conversational flows, prompt injection, model blind spots, misconfigured APIs, and weak session or authentication controls to exfiltrate data, bypass business logic, and erode user trust.

Accorian’s AI Chatbot Penetration Testing Services are designed specifically for LLM-powered and AI-augmented chat interfaces. Our testers combine deep experience in application and API security with AI-specific methodologies to evaluate your chatbot end to end: from the web UI and middleware to underlying LLM components, third-party integrations, and back-end data stores.

Our approach blends dynamic testing, AI-specific tooling, and threat modeling to help you identify and remediate issues that can lead to prompt injection, data leakage, abusive automation, or unauthorized access—while aligning with frameworks like OWASP Top 10 for Web, APIs, and LLM applications.

What’s Included in Accorian’s AI Chatbot Penetration Testing?

1. Planning & Scoping

• Define chatbot use cases, flows, integrations, and data sensitivity.

• Map architecture components: UI, middleware, APIs, LLM provider(s), data stores, and third-party services.

• Align testing scope with your risk appetite, roadmap, and compliance requirements (e.g., GDPR, CCPA, SOC 2).

2. Reconnaissance & Behavioral Mapping

• Interact with the chatbot to understand intent handling, guardrails, and escalation paths.

• Identify exposed endpoints, authentication flows, and session handling patterns.

3. Vulnerability Assessment – Traditional & AI-Specific

• Dynamic Application & API Testing:

o Web and API testing for OWASP Top 10 issues (injection, broken access control, XSS, insecure deserialization, etc.).

• Prompt Injection & Conversation Manipulation:

o Attempt jailbreaks, instruction overrides, and indirect prompt injection via integrated content sources.

• LLM-Specific Checks:

o Model inversion, data poisoning, information disclosure, and safety-guard bypass attempts.

• Data Handling & Privacy Review:

o Validate how prompts, logs, and conversation histories are stored, masked, or retained.

4. Exploitation & Attack Simulation

• Simulate real-world attacks against the chatbot stack, including:

o SQL/command/script injection via chatbot flows and APIs. o Privilege escalation and horizontal/vertical access control abuse. o Prompt-driven exfiltration of secrets, internal tools, or sensitive user data.

5. Tooling & Benchmarks Representative tools and techniques include (tailored to your environment):

• Nmap, Burp Suite, Metasploit, and other standard PT tools.

• AI-focused frameworks such as Giskard, Garak, and Protect AI where applicable.

• Testing aligned to:

o OWASP Top 10 for Web Applications o OWASP Top 10 for APIs o OWASP Top 10 for LLM Applications

6. Reporting & Remediation Support

• Detailed report of vulnerabilities, attack paths, and business impact.

• Clear, prioritized remediation guidance for engineering, product, and security teams.

• Optional read-out session with stakeholders to align on next steps and roadmap.