Okay here is the setup: Outlook 2007 POP/SMTP iPhone POP/SMTP Entourage 2008 POP/SMTP Webhost: DSL Extreme No other device/software is getting dupes except entourage 2008. Outlook is fine, iPhone is fine. Entourage, will all of a sudden download 500+ messages, as if it just connected to the server for the first time, resulting in a ton of dupes! Anyone with this experience or ideas? Entourage 2008 is on a laptop, so it'll connect to different networks. It's like connecting for the first time everytime, and it's pissing me off! reason why POP. Outlook 2007 has certain folders that does not want to be seen on the Entourage 2008, as well as Entourage 2008 has folders that doesn't wanna be seen on the outlook! And I don't know the dynamics of mixing a iMAP and a POP account, but it sounds like it'll screw things up pretty badly... especially with all the folders on the entourage. For example, if I made the entourage an imap account, and the outlook 2007 a pop account, will it download the folders from entourage?