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Simon Willison's Weblog

Release: datasette 1.0a29 Thoughts on GitLab’s workforce reduction A quote from James Shore Your AI Use Is Breaking My Brain TIL: Using LLM in the shebang line of a script Learning on the Shop floor A quote from New York Times Editors’ Note A quote from Andrew Quinn A quote from Luke Curley Release: llm-gemini 0.31 Tool: Big Words Behind the Scenes Hardening Firefox with Claude Mythos Preview Notes on the xAI/Anthropic data center deal Tool: GitHub Repo Stats Live blog: Code w/ Claude 2026 Vibe coding and agentic engineering are getting closer than I’d like Release: datasette-referrer-policy 0.1 Release: datasette-llm 0.1a7 Release: llm-echo 0.5a0 Granite 4.1 3B SVG Pelican Gallery A quote from Andy Masley April 2026 newsletter Research: TRE Python binding — ReDoS robustness demo Tool: Redis Array Playground A quote from Anthropic Sightings iNaturalist Sightings Codex CLI 0.128.0 adds /goal Our evaluation of OpenAI's GPT-5.5 cyber capabilities Quoting Andrew Kelley
GPT-5.5 prompting guide
2026-04-25 · via Simon Willison's Weblog
GPT-5.5 prompting guide Now that GPT-5.5 is available in the API , OpenAI have released a wealth of useful tips on how best to prompt the new model. Here's a neat trick they recommend for applications that might spend considerable time thinking before returning a user-visible response: Before any tool calls for a multi-step task, send a short user-visible update that acknowledges the request and states the first step. Keep it to one or two sentences. I've already noticed their Codex app doing this, and it does make longer running tasks feel less like the model has crashed. OpenAI suggest running the following in Codex to upgrade your existing code using advice embedded in their openai-docs skill: $openai-docs migrate this project to gpt-5.5 The upgrade guide the coding agent will follow is this one , which even includes light instructions on how to rewrite prompts to better fit the model. Also relevant is the Using GPT-5.5 guide , which opens with this warning: To get the most out of GPT-5.5, treat it as a new model family to tune for, not a drop-in replacement for gpt-5.2 or gpt-5.4 . Begin migration with a fresh baseline instead of carrying over every instruction from an older prompt stack. Start with the smallest prompt that preserves the product contract, then tune reasoning effort, verbosity, tool descriptions, and output format against representative examples. Interesting to see OpenAI recommend starting from scratch rather than trusting that existing prompts optimized for previous models will continue to work effectively with GPT-5.5. Tags: ai , openai , prompt-engineering , generative-ai , llms , gpt