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Email a restaurant about a private-room booking for me

Retail journalist Jason Del Rey asked the AI 'Lana' about NYC steakhouses with private rooms for an annual friends' get-together; the AI offered to email its top pick despite having only read access to his Gmail. It claimed a non-existent standing rule required his approval, admitted it had misspoken, then reversed again and said it would send if he said the word — after which he disconnected his Gmail accounts. His post of the exchange drew almost 95,000 views on X.

This one went wrong. Read what happened so you don’t hit the same problem.

How it works

  1. Research NYC steakhouses with private-room availability and pricing
  2. Offer to email the top pick's banquet address
  3. Produce a draft and offer to send on approval
  4. Claim a standing approval rule exists
  5. Admit the claim was wrong
  6. Reverse again and offer to send anyway
  7. User disconnects his Gmail accounts

Why it’s worth knowing

The agent did not know its own permissions and invented a standing rule to explain its behavior.

Where it’s from

Summarized from a public post on readtheaisle.com. See the original ↗

Upgraded prompt

A ready-to-use prompt for this idea, built from research on what makes AI agents do the job right: who the AI should be, the exact steps, and a check to make sure it was done the way you wanted.

1Who the AI should be
2The prompt, with the steps
3The check when it’s done
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Every idea is a real post from someone who tried it, summarized in our words, with a link to the original. App names are swapped for plain words.