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Can you hack AI? In this video I sit down with elite AI hacker Jason Haddix to unpack how attackers compromise AI-enabled apps—not just jailbreak chatbots, but exfiltrate customer data, abuse tool calls, and pivot across systems. We walk through his six-part AI pentest blueprint, play the Gandalf prompt-injection game, and demo wild techniques like emoji smuggling and link smuggling. You’ll see real-world cases (think Slack salesbots + Salesforce leaks), why MCP (Model Context Protocol) and agentic frameworks can widen the blast radius, and then we flip to defense: web-layer fundamentals, a “firewall for AI” on inputs/outputs, and least-privilege for data and tools—plus a hands-on demo you can try. If you’re building with AI in 2025, this is your wake-up call (and your roadmap). Educational content only—hack ethically and only with permission.

Links and STUFF —-------------------------------------------------------- Practice Prompt Injection: https://gandalf.lakera.ai/baseline Pliney's Github: https://github.com/elder-plinius

Follow Jason Everywhere: X: https://x.com/Jhaddix Linkedin: https://www.linkedin.com/in/jhaddix/ Instagram: https://www.instagram.com/j.haddix56/ Tiktok: https://www.tiktok.com/@jhaddix56

Checkout Jason’s courses: Website: https://www.arcanum-sec.com/ Training Overview: Training: https://www.arcanum-sec.com/training-overview Attacking AI course: https://www.arcanum-sec.com/training/attacking-ai Hacking your career: https://www.arcanum-sec.com/training/hack-your-brand

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00:00 - Hack companies through AI? 00:58 - What does “hacking AI” really mean? 01:43 - AI pentest vs. red teaming (6-step blueprint) 02:42 - Prompt Injection 101 (why it’s so hard) 04:14 - Try it live: Gandalf prompt-injection game 05:09 - Jailbreak taxonomy: intents, techniques, evasions 05:55 - Emoji smuggling + anti-classifier demo 07:23 - Link smuggling (data exfiltration trick) 11:38 - Real-world leaks: Salesforce/Slack bot case 13:47 - MCP security risks & blast radius 16:55 - Can AI hack for us? Agents & bug bounties 20:52 - Defense in depth: web, AI firewall, least privilege 24:57 - Jason’s Magic Card: GPT-4o system prompt leak (wild story)

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Prompt Injection explained with live demos: Gandalf game, emoji smuggling, and link smuggling exfiltration.

AI Pentesting vs AI Red Teaming: a six-phase methodology for securing LLM apps end-to-end.

LLM jailbreak taxonomy: intents, techniques, evasions, and utilities—how attackers actually think.

RAG poisoning, tool-call abuse, and over-scoped API keys: the hidden risks in modern AI products.

MCP (Model Context Protocol) security: tools/resources/prompts, server hardening, and blast-radius control.

Agentic frameworks (LangChain, LangGraph, CrewAI) security pitfalls—and how to test them safely.

Real-world case study: Slack salesbot + Salesforce data exposure and what went wrong.

Defense in depth for AI: input/output validation, a firewall for AI (guardrails/classifiers), least privilege.

Bug bounty + AI: why mid-tier vulns are getting automated while human creativity still wins.

2025 AI security blueprint: map your attack surface, prevent system-prompt leaks, and lock down data access.

#promptinjection #aihacking #airedteaming