Powering Duemilanove via VIN and external 12V power supply and USB power problem

This data sheet may tell us what is happening

The datasheet has no information about Vout being greater than Vin - everything is in terms of Vin being Vout +3V for example.

Looking at the schematic and how it is applied in the duemilanove, it looks like a zener that is supposed to provide some protection may be the path that lets Vout appear at Vin.