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Find my Vegas to San Diego flights and use my Amex points well

Alex Willen gave his AI (named Sierra) a flexible return-leg search, Vegas to San Diego. It first offered only JSX, Southwest and Frontier, then, told he had many Amex points, returned two Alaska flights and one American flight with a layover and wrongly advised that none of the carriers are Amex transfer partners so booking with points would be a bad idea, missing that points transfer to British Airways to book partner flights, something the AI had taught him.

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

How it works

  1. Search the route (only 3 carriers offered)
  2. User adds Amex points preference
  3. The AI returns Alaska/American options incl. a layover
  4. The AI wrongly says no transfer partners exist and points booking is a bad idea

Why it’s worth knowing

The agent's confident points advice was exactly backwards: the standard BA transfer workaround is the first thing a points-savvy human would check.

Where it’s from

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

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