Simon Willison — 2026-05-21#

Highlight#

The major news today is the official announcement of Datasette Agent, merging Simon’s three years of work on the LLM library with Datasette to create an extensible, conversational AI assistant for querying data. It represents a huge milestone for his ecosystem, opening the door for users to naturally interrogate their databases and easily build custom tools using a new plugin architecture.

Posts#

Datasette Agent Simon officially announced Datasette Agent, a conversational AI interface that lets users ask questions of the data stored in Datasette. The post features a live demo using Gemini 3.1 Flash-Lite to successfully query a blog database to find a bird-watching record. He highlights a growing plugin ecosystem—including charts, image generation, and sandbox execution—and notes that tools like Claude Code and OpenAI Codex are proving excellent at writing these extensions. Looking ahead, Simon teased a major refactor for his LLM library, a Claude Artifacts-style plugin, and a personal AI assistant named “Claw” built using his older Dogsheep tools.