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In practice, however, user queries are often underspecified, forcing models to infer unstated assumptions that may misalign with the actual user intent. Existing prompt engineering guidelines aim to mitigate this issue, they are typically generic and task-agnostic, limiting their practical utility. Additionally, existing guidelines are formed manually and in a non-systematic way. To this end, we study prompt guideline optimization: the problem of automatically generating task-specific guidelines that help write better-specified prompts for a given task and model. 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