Coming late 2026

Assume It Will Fail

A field guide to AI security for founders and builders shipping fast.

Prompt injection, leaked credentials, rogue automations, and model behavior drift are now product risks. This book gives you practical controls that fit real startup velocity.

The book is being written in public. Read the 13-part series free, or join the waitlist for launch updates, early access, and release pricing.

Join the waitlist
Seth Black
Assume
It Will
Fail.
AI Security Field Guide
Vol. II ยท 2026

Who it is for

Founders, lead engineers, and small teams putting LLMs, agents, and RAG into real products. You do not have a security department. You do have customer data, API keys, and a model that will cheerfully follow instructions hidden in a PDF. The starting assumption is in the title: the model, the tool call, or the prompt will fail eventually, so design for the blast radius.

What it covers

Access and isolation

Least privilege for agents, isolating tools and tenants so one prompt cannot reach everything, and locking down MCP servers.

Data that leaks

RAG pipelines and vector databases that expose documents, and a proxy that scrubs SSNs, card numbers, and PII before a prompt leaves your network.

Your own dev tooling

Code assistants, MCP devtools, CI bots, AI in the deploy pipeline, and the shadow AI your team installed without asking.

Testing and response

Human review that is more than a rubber stamp, red-teaming your own AI, and logging and incident response for systems that fail probabilistically.

Regulation

Data minimization for agents under GDPR and the EU AI Act, and how not to become a non-compliant HIPAA data processor by accident.

Read the series free

The book grows out of this 13-part series. Each post stands on its own.

  1. Principle of Least Privilege in the AI Age
  2. Isolating Tools, Agents, and Tenants So One Prompt Can't Nuke Everything
  3. How to Actually Secure MCP (Model Context Protocol)
  4. RAG, Vector DBs, and Leaky Knowledge Bases
  5. Building an LLM Proxy That Scrubs SSNs, Credit Cards, and PII Before It Leaks
  6. Securing Dev-Facing AI: Code Assistants, MCP Devtools, and CI Bots
  7. AI in CI/CD: Let the Bot Write, But Make It Earn the Deploy
  8. Shadow AI: Unapproved Tools, Extensions, and Copy-Paste Ops
  9. Human in the Loop, Not Human as Rubber Stamp
  10. How to Red-Team Your Own AI
  11. Logging, Monitoring, and Incident Response for AI Systems
  12. GDPR, EU AI Act, and Your AI Stack: Data Minimization for Agents
  13. HIPAA, PHI, and AI: How Not to Accidentally Become a Non-Compliant Data Processor

Related: the AI security assessment, and the rest of Seth's books.

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