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At my office, I have iTunes set up for listening to music while I program. Every now and then I'll hear a song on someone else's playlist, and want to purchase it. Only problem is transporting it to and from home.

What I'd like to do is set up iTunes on my laptop at home to communicate with iTunes on my workstation in my office. Both machines are running OSX. I have a VPN which I log into, but the computers are on different subnets, and thus it does not work.

Home Network: Work Network: VPN Address: (I'm not sure what the subnet is on this, but it shows up as interface utun0 on the home machine).

The VPN is working as I can access my workstation, but of course I cannot see the machine in iTunes Home Sharing. Is there a way to add a route over the VPN so that I can access this?

I don't have any problem with CLI, adding routes, etc.

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I have a similar setup, but use VPN differently - My router provides to the local network, and I have OpenVPN running which bridges clients to the router - the router still handles DHCP and there is no NAT, so there is no way for one client to tell if another client is connected directly to the router or not (except perhaps for ping latency). Both my desktop and laptop can share their libraries without a problem, though I use a home server running Firefly (a DAAP server) to distribute my music over the network, which also shows up as a shared library just fine. I haven't had reason to test/try home sharing (because of my server), but I highly doubt it would have trouble with this setup.

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Because it is a corporate VPN server, I can't really do that. =-[ – Jack M. Jun 29 '10 at 23:05
@Jack Unless you're unable to install programs on your home and office computers, you can connect a single computer to as many VPNs as you want as long as they're all on different subnets. iTunes' sharing will only function if the computers are on the same subnet. I suspect that only your home computer is on a VPN, and your work computer is simply connected to the network (but on a separate subnet). – Darth Android Jun 30 '10 at 5:19

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