RE: Dynamics Nav 2013 Role Tailored Client over VPN
I have the same problem as well.
I think that problem is with user domain authenticaton on database over VPN, I did not spend so mouch time but I made test with configured NavUserPassword service over the same VPN and is working, with domain autentification over same VPN it is not working.
What I did is to authenticate on domain and pretended that my computer is not part of that domais,so I create one more icon on my desktop and name the icon VPN Dynamics NAV, than put in target this path:
C:\Windows\System32\runas.exe /user:"yourdomain\yourusername" /netonly "C:\Program Files (x86)\Microsoft Dynamics NAV\90\RoleTailored Client\Microsoft.Dynamics.Nav.Client.exe"
In the path change yourdomain\yourusername and save the target (Iam using NAV 2016 so you can change path for NAV 2013 if still using that version).
Than you will be prompt for domain password and after that NAV over VPN is working.