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Find the map/territory gap BEFORE it gets expensive. Invoke when starting a non-trivial task in unfamiliar territory (new module, new technology, work the user has not done before), when acceptance criteria are "I'll know it when I see it", when the user struggles to describe what they want, or when a long-horizon task came back wrong and a blind retry is tempting. Not for typo-level fixes or tasks with fully objective acceptance criteria.