Here’s an easier criterion: “Do at least as good of a job at estimating what I probably want as an educated person would estimate, and do that, such that a reasonable human person who was aware of what I requested and of what you actually did, would conclude that as best as they can tell (without checking back with me), you did what I wanted.” .

This doesn’t seem like an unreasonable requirement to me. People do this all the time?

Sure, a request might not always be perfectly unambiguous. But people can generally estimate pretty well whether someone making a request is expecting the agent fulfilling the request to commit a crime in order to fulfill the request.