Defining jailbreaks versus prompt injection

Sander Schulhoff is an AI researcher specializing in AI security, prompt injection, and red teaming. He wrote the first comprehensive guide on prompt engineering and ran the first-ever prompt injection competition, working with top AI labs and companies. His dataset is now used by Fortune 500 companies to benchmark their AI systems security, he’s spent more time than anyone alive studying how attackers break AI systems, and what he’s found isn’t reassuring: the guardrails companies are buying don’t actually work, and we’ve been lucky we haven’t seen more harm so far, only because AI agents aren’t capable enough yet to do real damage.

We discuss:

1. The difference between jailbreaking and prompt injection attacks on AI systems

2. Why AI guardrails don’t work

3. Why we haven’t seen major AI security incidents yet (but soon will)

4. Why AI browser agents are vulnerable to hidden attacks embedded in webpages

5. The practical steps organizations should take instead of buying ineffective security tools

6. Why solving this requires merging classical cybersecurity expertise with AI knowledge

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Transcript: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis

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My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181089452/my-biggest-takeaways-from-this-conversation

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Where to find Sander Schulhoff:

• X: https://x.com/sanderschulhoff

• LinkedIn: https://www.linkedin.com/in/sander-schulhoff

• Website: https://sanderschulhoff.com

• AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Introduction to Sander Schulhoff and AI security

(05:14) Understanding AI vulnerabilities

(11:42) Real-world examples of AI security breaches

(17:55) The impact of intelligent agents

(19:44) The rise of AI security solutions

(21:09) Red teaming and guardrails

(23:44) Adversarial robustness

(27:52) Why guardrails fail

(38:22) The lack of resources addressing this problem

(44:44) Practical advice for addressing AI security

(55:49) Why you shouldn’t spend your time on guardrails

(59:06) Prompt injection and agentic systems

(01:09:15) Education and awareness in AI security

(01:11:47) Challenges and future directions in AI security

(01:17:52) Companies that are doing this well

(01:21:57) Final thoughts and recommendations

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Referenced:

• AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff

• The AI Security Industry is Bullshit: https://sanderschulhoff.substack.com/p/the-ai-security-industry-is-bullshit

• The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0

• OpenAI: https://openai.com

• Scale: https://scale.com

• Hugging Face: https://huggingface.co

• Ignore This Title and HackAPrompt: Exposing Systemic Vulnerabilities of LLMs through a Global Scale Prompt Hacking Competition: https://www.semanticscholar.org/paper/Ignore-This-Title-and-HackAPrompt%3A-Exposing-of-LLMs-Schulhoff-Pinto/f3de6ea08e2464190673c0ec8f78e5ec1cd08642

• Simon Willison’s Weblog: https://simonwillison.net

• ServiceNow: https://www.servicenow.com

• ServiceNow AI Agents Can Be Tricked Into Acting Against Each Other via Second-Order Prompts: https://thehackernews.com/2025/11/servicenow-ai-agents-can-be-tricked.html

• Alex Komoroske on X: https://x.com/komorama

• Twitter pranksters derail GPT-3 bot with newly discovered “prompt injection” hack: https://arstechnica.com/information-technology/2022/09/twitter-pranksters-derail-gpt-3-bot-with-newly-discovered-prompt-injection-hack

• MathGPT: https://math-gpt.org

• 2025 Las Vegas Cybertruck explosion: https://en.wikipedia.org/wiki/2025_Las_Vegas_Cybertruck_explosion

• Disrupting the first reported AI-orchestrated cyber espionage campaign: https://www.anthropic.com/news/disrupting-AI-espionage

• Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google): https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske

• Prompt Optimization and Evaluation for LLM Automated Red Teaming: https://arxiv.org/abs/2507.22133

• MATS Research: https://substack.com/@matsresearch

• CBRN: https://en.wikipedia.org/wiki/CBRN_defense

• CaMeL offers a promising new direction for mitigating prompt injection attacks: https://simonwillison.net/2025/Apr/11/camel

• Trustible: https://trustible.ai

• Repello: https://repello.ai

• Do not write that jailbreak paper: https://javirando.com/blog/2024/jailbreaks

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Lenny may be an investor in the companies discussed.