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Originally Posted by Brian View Post
Layering the VPN on top of that sounds like a lot of work for a little bit of additional benefit...
Well, for OmniFocus, perhaps, but one might be doing it to secure all of the other traffic from prying eyes at the coffee shop, library, etc.

RJW, can you provide some more details about exactly how you are doing this?

One approach you could take is to keep the VPN, but switch to using the Omni Sync Server instead of the Bonjour sync. Then you don't have to wrestle the VPN software to get all of your traffic sent the right way, and as a bonus, you can sync even when the two devices aren't on the same network.