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I wrote earlier about your machine being the attack surface, which covers the local side: leftover credentials, permission flags, untrusted input. This is the other side, the moment an agent reaches out and touches an external system. I hit three of these this month. Same problem each time: once the thing ships you can’t pull it back, and the mistake lands where the client can see it.
If the pronoun has more than one referent, don’t touch anything that sends notifications
I dictated a line that translates to “confirmed it with him on IG, change the calendar.” The agent decided who “him” was, picked a client, and moved that person’s calendar invite, with send-updates=all attached. I had meant someone else.
The rollback made it worse. The moment the date went back, that same client got a second update notification. One misreading, and what the client saw was two baffling reschedule emails.
Lesson: when a pronoun has more than one possible referent, confirm who it is before touching an external system. Calendar invites and email especially, since neither can be recalled. The costs are lopsided. Asking one more question isn’t in the same weight class as an error the client can see.
Reply-all carries over the people the other side added themselves
A collaborator replied and cc’d three of their own colleagues. I built the draft with --reply-all, and the recipient list went from two people to six. The flag wasn’t wrong, that’s exactly what it does. I just never looked at what the list had turned into before it went out.
Two things here. One is privacy: scope and fees end up in front of more people, and I didn’t know those three at all. The other is signal. Pulling people into a thread means something, it tells you who’s involved, and it’s worth a look before you decide how to write.
Lesson: once an outbound draft exists, read the actual To and Cc list before sending, then decide whether to drop the extra recipients. Don’t assume the recipients match the previous message just because you’re replying to it.
Internal notes on a hold event ship with the invite
I put a hold on the calendar and used the notes field for my own read on the situation. The event later sent an invite, and the notes went to the client’s inbox with it. I rewrote it as an outward-facing version afterward, but the first one was already gone.
Notes on a calendar event don’t feel like email. They feel like your own scratch space. The moment there’s an invitee, they’re an outward-facing field.
Lesson: the moment there’s an invitee, that field is outward-facing. Rewriting it later doesn’t pull the first one back.
All three have the same shape. The step the agent executed had no bug in it. What broke was the door between that step and the external recipient, the one I never looked through.