Hi,
Most likely they are in different subnet mask and MMW blocked external access. Check MMW DLNA Server settings.

Sorry to necro the thread, but I'm trying to make this work using OpenVPN. I've got a vpn connection (device IP: 10.1.0.10) to my home router (10.2.1.1) and can ping the server that hosts mmw (10.2.1.55). However, MMA can't locate the server; when I hit "Sync" it just searches for server indefinitely.

I see that there's some issues with multicast over TAP connections on OpenVPN, but I'm using TUN anyways. OpenVPN is set to push the LAN to clients and allow client-client communication (also to do DNS). In short, everything should be working.

Any ideas on what to look for or how to troubleshoot?

And as I understand it, the way DLNA finds servers is that the DLNA client does a broadcast on the local network, and DLNA servers respond with their information. So unless you are on a VPN to your home network (ie OpenVPN), the broadcast would never be routed outside the local network to your home network.

Rather, you would have to enter the information - see:
http://www.ventismedia.com/mantis/print_bug_page.php?bug_id=8100
http://www.mediamonkey.com/wiki/index.php/WebHelp:Setting_UPnP/DLNA_Media_Servers/4.0
http://www.mediamonkey.com/forum/viewtopic.php?f=20&t=64584&p=332108#p332108
http://forum.mediamonkey.com/viewtopic.php?f=20&t=68470#p350977

[quote="Balthazar2k4"]What I want to do is run MediaMonkey on my home media server and then feed my laptop at the office running MediaMonkey with my remote music library so I can sync my AK100 when I travel.[/quote]
Apart fom the client problem Lowlander mentioned there are at least two more disadvantages:

1) Syncing from your home to your office over the internet probably will be very slow as the upstream rate of your internet connection at home will be the speed limit.

2) You'll have to open a port in your router which is potentially dangerous unless your router can establish a VPN.

An alternative might be to upload your tracks to a service like Google Music or Amazon's Cloud Player which will give you access to them from all over the world.

Thanks Lowlander. Is there an alternative way to do what I want? It seems to me that given the current state of technology and the ability to stream from services like Plex across the internet that remote device syncing wouldn't be a giant hurdle.

If you have a client that can connect to a specific IP (not aware of a desktop client that can) you can share DLNA over the internet (with setting the right permissions in your router). Do note that DLNA is meant to be used within the same network.

Maybe this is a dumb question, but I am only starting to investigate MediaMonkey's potential for this application. What I want to do is run MediaMonkey on my home media server and then feed my laptop at the office running MediaMonkey with my remote music library so I can sync my AK100 when I travel. Is this possible?

Thanks in advance.