Why does the A.I. part of the situation make social engineering scarier?
2) Actual Risk. Software has bugs. When software is meant to give out some subset of data it is not unknown for it to give out more data than it means to. A human PA may make mistakes and blurb something that he/she shouldn't have, but he/she also knows when to stop giving out information. If a particularly trained AI starts leaking out information, it will happily do so for user after user after user.
[1] http://en.wikipedia.org/wiki/HAL_9000 [2] http://futurama.wikia.com/wiki/Project_Satan