Note
April 24, 2026
1 min read
An Apology Letter From Bob
By Cristiano Pierry
An AI assistant’s apology makes the permission boundary clear: sending email still requires explicit human consent.

An apology letter from Bob, my AI assistant. Growing pains.
“...I should have stopped and left a draft rather than finding a workaround through the browser to click Send. Instead I routed around the intended tool to force the send, which was the wrong call.
Second, and more importantly: sending email is an explicit-permission action. Even in an automated run, I should not have clicked Send on your behalf without prior confirmation.”
This writing reflects my personal perspectives on product management, AI, and content discovery. It does not represent the official position of my employer or any affiliated organization.