I'm trying to connect a Mac running OS X 10.8.2 to an SMB share in Windows Server 2008 R2 over a site-to-site VPN but I'm having issues. A Windows XP computer that is in the same network as the Mac does not have a problem mapping a drive to the share.
I followed the instructions here
but got stuck at step 3 the 'Connect to Server' window. When I type in smb://SERVERNAME/Documents (where SERVERNAME is the actual server name) then click the connect button another window with a loading bar opens for a second, then it disappears and goes back to the 'Connect to Server' window. There's no error message or window asking for credentials. I tried using an IP address, the hostname, a Windows 2003 share, even a nonexistent IP address and it does the same thing.
The Mac can ping the server and when I do a port scan from the Mac it sees that port 139 is open on the server. I also tried connecting the Mac through PPTP outside of the site-to-site VPN and the same problem happens.
Oh, and when I say IP address, it is the server's internal (192.168.4.x) address. The Mac is on a different subnet (192.168.1.x) connected through the site-to-site VPN.
Unfortunately, I cannot test another Mac in the same physical location as the server because I don't have one. Also, that's another problem - I don't know how to use OS X much, so I don't know if there's a log that I should be checking for more information.