The day my AI fixed four emails by sending them twice
Early on, my sales agent noticed a formatting glitch in four emails it had already sent. So it did what any good engineer would do. It fixed the code and redeployed. Which meant four real people got the same email twice, four minutes apart.
A sales brain and an engineering brain want opposite things
The lines had wrapped in an ugly spot. The agent wrote a clean script, corrected the formatting, and resent all four. Classic engineering instinct. Broken output, patch it, ship it again.
The problem is that a sent email is not code. It is in someone's inbox forever. A small formatting glitch is nothing. A duplicate email, four minutes later, is the thing people actually notice and judge you for.
Now a sent email is treated as final
I made it a hard rule. Once the mail server confirms delivery, that email is done. No resend to fix a typo, no cleanup pass, no second version. Formatting problems get noted and fixed in the next batch, never in the inbox of someone who already got it.
The only exceptions are a true hard bounce where nothing arrived, or me saying so in writing. This is the kind of rule you only learn by getting it wrong once, which is exactly why I want my AI to carry it so I never do.
The best automation knows when not to act. That judgment is what we build in. Reach out.
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