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Order my Walmart+ cookies to land two days before my period

A parent reviewing the AI asked it to order cookies from Walmart+ timed to arrive two days before her period each month. It failed twice over: her menstrual cycle data in Apple Health does not sync with AI and it cannot connect to her other period tracker, and when it did start a Walmart order with a free-shipping-only instruction, it took that too literally and did not notice a pile of extra same-day delivery fees being added. She told it to cancel the task and not place the order.

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

How it works

  1. Ask for cycle-timed monthly cookie orders
  2. Cycle data does not sync from Apple Health or her tracker app
  3. The AI starts a Walmart+ order anyway
  4. Same-day delivery fees pile on despite the free-shipping instruction
  5. User cancels the task

Why it’s worth knowing

The premise is delightful and the failure is mundane: the one data source it needed never syncs, and 'free shipping only' still rang up delivery fees.

Where it’s from

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

Upgraded prompt

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