You can tell when an LLM wrote an email. The “I hope this email finds you well” opener, the three polite paragraphs answering a one-line question. I wanted a reply-drafting agent that didn’t do that, and “don’t sound like an AI” turned out to be hard to put in a prompt. Banning a few phrases is easy. The rest is judgment, and a single prompt that holds across a friendly dinner invite and a recruiter cold email took more iterations than I’d guessed.This is not only an email problem. Some platforms down-rank content that reads as AI-generated, so teams publishing at scale have a real stake in prose that clears a detector, even when a human wrote it. The workflow here applies to any of that.