Why Social Engineering Now Works on Machines

Ian Webster built PromptFoo after watching 200 million Discord users systematically dismantle his AI agent—now Fortune 10 companies pay him to break theirs before customers do. The "lethal trifecta" sounds academic until you realize it's already happening: untrusted input plus sensitive data plus an exfiltration channel equals the security incident that just cost a SaaS company its multi-tenancy guarantees. Webster's red-teaming agents don't use signatures—they have 30,000 conversations with your system, socially engineering their way past guardrails the same way a teenager with emojis convinced ChatGPT to leak data, except his tools find the vulnerability before your users become the pen testers. Follow Ian Webster on X: https://x.com/iwebst Follow Joel on LinkedIn: https://www.linkedin.com/in/3448827723723234/ Check out everything a16z is doing with artificial intelligence here, including articles, projects, and more podcasts.   Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.