Promptfoo has developed an advanced red teaming tool designed to bolster the security of Large Language Model (LLM) systems by simulating sophisticated attacks. The evolution of red teaming has progressed from simple static prompts to dynamically generated attacks that consider the context of the target application. Promptfoo's system enhances traditional penetration testing techniques by incorporating deep reconnaissance, strategic planning, adaptive attack execution, and persistent memory, allowing for a comprehensive understanding of the target system and enabling iterative exploitation strategies. The tool prioritizes attack vectors based on business impact and system vulnerabilities, ensuring that attacks are aligned with critical business objectives. By bridging the gap between LLM vulnerability research and practical application, Promptfoo aims to set a new standard for enterprise-grade LLM security, offering a system that continuously learns and adapts through a process of real-time monitoring and replanning.