Please excuse if this question has been asked many times before. I have just purchased a 2008 Prius and my iPhone 3GS is added as a valid bluetooth device but the phonebook will not transfer. The phone disconnects when I try to start the transfer and when I try to reinitialize a connection from my phone eventually the transfer fails. Any help would be appreciated. I have searched the forum but I am having little luck finding helpful posts.
I think you are SOL w/the iPhone (I had a 3G and now the 4) and the 2nd gen Prius. See http://priuschat.com/forums/gen-ii-prius-audio-electronics/91645-gen-2-iphone-4-a.html#post1293093. If anyone succeeds on a Gen 2, I'd love to hear about it and also hear about what version of nav DVD they have. I had no trouble transferring ALL my contacts in one fell swoop from the iPhone 3G to a Lexus HS 250h which has a newer gen nav system.
Best solution on a Gen 2 Prius is to replace the radio with a modern double din unit. I put a Sony XAV-AX1000 radio in mine that has modern Bluetooth as well as CarPlay.