Most well-educated people won't. A well trained AI can behave pretty close to a well-educated person in common sense.
Possibly related: confidence schemes and magic tricks. As the adage goes, one of the best way to make a magic trick work is to make it much more elaborate, and/or invest much more in its setup or execution, than any reasonable person would ever expect.
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[0] - A fake package delivery mail that, by chance, came at the exact time you expected one for a real order, and with very similar details. Or fake corporate OneDrive deletion e-mail that came just after your system was migrated in a process that could involve deletion of old OneDrive files.