Jailbreaking Black-Box LLMs Using Promptfoo: A Complete Walkthrough

Promptfoo is an open-source framework designed to help developers test large language model (LLM) applications for security, privacy, and policy risks by enabling the discovery and rectification of critical LLM failures. It offers tools for conducting red team exercises, third-party penetration tests, and bug bounty programs, significantly reducing the time needed for manual prompt engineering and adversarial testing. The blog outlines how to use Promptfoo's red team tool in a black-box LLM security assessment, with a focus on a case study involving Prompt Airlines. The process involves configuring Promptfoo to launch adversarial attacks against LLM endpoints, identifying vulnerabilities such as the chatbot's susceptibility to jailbreaking techniques like impersonation and character roleplay, while also noting the failure of leetspeak and base64 encoding queries. By automating the generation and evaluation of adversarial payloads, Promptfoo can quickly identify LLM vulnerabilities, allowing researchers to refine their testing strategies efficiently.