My old (great, reliable — until it got wet) TomTom One series finally died a while back, and the android phone isn’t cutting it in areas without cell coverage so I finally upgraded to a new Via series. Unfortunately, it refused to talk to OSX at first. The status icon would say “Connecting” and the right part number would show up in their web interface, but I was unable to associate the device with my account or add any updates.
Luckily I stumbled on a solution: Instead of USB mass storage like the old models, the VIA seems to show up as a network interface. As a result, OSX wants the new “network interface” to be “configured”. I was able to simply open the network settings panel choose “TomTom” and click apply with the “mytomtom” software running and the device connected almost instantly. The TomTom device should (it seems) be set to get a DHCP address (hopefully the default).
If it works the same on Windows machines, I’d imagine that the Windows Firewall and any 3rd party firewall software would have the potential to cause similar symptoms. Windows users might want to check into that.