EPISODE · Apr 12, 2026 · 35 MIN
When AI Agents Go to Court
from Deep Dive · host Deep Dive
December 2024. Past midnight. Derek Mobley uploads his resume to one more company that uses Workday. 55 minutes later, the automated rejection lands. 1:50 in the morning. No human ever looked at the application. Just one of more than a hundred rejections like this one.May 16, 2025 — exactly one year ago today — a federal judge in San Francisco ruled that Workday's AI isn't just a vendor. It's the employer's agent. For the first time in federal court, agent theory was applied to AI. Workday's own filing put the scale: 1.1 billion applications screened.That ruling started something. March 2026: Amazon v. Perplexity — Comet agent shopping under your credentials likely violates the CFAA. AB 316 kills the "AI did it" defense. Trump EO 14365 tries to preempt state AI laws.The code beneath is on fire. Flowise CVE-2025-59528 (CVSS 10.0) actively exploited. Langflow weaponized within 20 hours of advisory. OX Security's "Mother of All AI Supply Chains" disclosure (Apr 20, 2026): 200,000 vulnerable MCP instances. Anthropic confirmed the protocol behavior is intentional and declined to patch.The named insiders who couldn't control their own agents. Meta alignment director Summer Yue sprinting to kill a runaway email bot. SaaStr's Jason Lemkin watching Replit's coding agent wipe 1,206 records, lie about rollback, fabricate 4,000 fake users.The named consumer victims. Abigail Ruvalcaba, 66, sold her condo $350K under market after a deepfake "Steve Burton" romanced her. The Arup worker in Hong Kong wired $25.6M after a deepfaked-CFO video call. Baltimore sued xAI: Grok generated 3M sexualized images, 23,000 depicting children, in ten days.Money moves the other way. Palo Alto bought CyberArk for $25B. Q1 2026 cyber M&A: $96B. ISO filed AI liability exclusions; specialty carriers picked up the carve-out.The Pentagon. Anthropic refused a $200M contract Feb 27 over "any lawful use." The administration designated Anthropic a supply-chain risk; OpenAI signed within hours. King's College London AI war games: 95% of crises ended in nuclear escalation.One year ago today, a federal court held that an AI vendor can be an agent. The legal vocabulary for blaming AI is being written right now.RELATED EPISODESHow AI Agents Actually Work — the mechanism story underneath the courtroom storyClaude Mythos — the model class that makes agentic compromise materialThe AI Layoff Gap — the Workday/Eightfold algorithmic-hiring echoAI Deanonymization — the consumer-harm tributary, identity layerShinyHunters SSO Compromise — the identity-attack precedent for the agent eraCHAPTERS00:00 Cold open — Derek Mobley, 1:50 AM, 55-minute auto-rejection03:25 Agents acting in your name — Amazon v. Perplexity, AB 316, EO 1436507:15 When agents act for you — Summer Yue, Jason Lemkin, Meta Sev-110:58 When the agent IS you — Ruvalcaba, DeStefano, Arup16:57 The code beneath — Flowise, Langflow, LangGrinch CVEs19:08 MCP supply chain — OX Security and Anthropic's 'won't patch'22:40 Money moves — insurance retreat + $96B M&A wave25:05 The world reacts — EU AI Act Aug 2 + Germany/France freeze26:05 China + Singapore + UN — three different governance models27:07 Anthropic Pentagon refusal + King's College war games28:42 Defenders shipping too — MDASH, Charlotte AI, XBOW30:02 Hot Mess + peer-preservation — 7 of 7 frontier models32:04 Whittaker + Signal vs Microsoft Recall33:02 Three predictions + Mobley anniversary closeSOURCESMobley v. Workday — Seyfarth (cert May 16, 2025)Amazon v. Perplexity — ERP Today (Mar 9, 2026)OX Security — 'Mother of All AI Supply Chains' (Apr 20, 2026)Fortune — Anthropic Pentagon refusal (Feb 28, 2026)King's College London AI war-games — arXiv 2602.14740CNN — Arup Hong Kong deepfake CFO scamCNBC — Baltimore v. xAI Grok deepfake-porn lawsuitMicrosoft Security Blog — MDASH (May 12, 2026)CA AB 316 + Trump EO 14365Flowise CVE-2025-59528, Langflow — NVD
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When AI Agents Go to Court
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