i run a small B2B tool with ~50 customers. agent drafts support replies that land in my gmail drafts with an [Agent-drafted] tag so i can review before sending. 95% of the time, fine. wednesday was not that 5%.
customer emailed in hot about a failed integration. real grievance, fair anger, typed in all caps in two places.
agent drafted a reply. landed in my drafts around 6:47am. i was half-asleep, skimmed it. it looked serious and urgent and acknowledged the problem. hit send.
her reply came in 4 minutes later. angrier.
i went back and re-read what i'd sent. the agent had matched her tone. not mirrored word-for-word, but matched the register. short sentences, urgency, one CLARIFYING CAP for emphasis. the message was substantively fine. the tone was combat.
had to send a follow-up apologizing specifically for the tone of my prior message. which i hadn't written. explained this to her. she laughed. we're fine now.
went back to the agent's CONVENTIONS.md and added a single line: if incoming message is upset, anxious, or angry, draft in calm de-escalating tone regardless of tone-matching defaults.
has worked fine since.
the meta lesson: tone-matching is a default behavior in these agents and nobody tells you. most of the time it's nice. the agent writes warm to warm people, professional to professional people. but with an upset person, the polite thing is to break the mirror, not reinforce it. i had never thought about this until an AI i set up made the mistake i would never have made myself.
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