Simon Willison 4/25/2026

GPT-5.5 prompting guide

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This article provides a comprehensive guide on prompting OpenAI's GPT-5.5 model, based on official recommendations. It highlights a key trick for applications that take time to respond: sending a short user-visible update before tool calls to improve user experience. The article also covers migration strategies, advising developers to treat GPT-5.5 as a new model family rather than a drop-in replacement, and to start with a fresh baseline prompt. It includes practical tips for rewriting prompts and tuning reasoning effort, verbosity, and output format.

GPT-5.5 prompting guide

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