SMB – Syntax for Accessing Windows Shares via Alternative Ports

The minimum needed to access Windows or Samba shares over a network is port 139 TCP - I've used this to tunnel Samba connections through SSH connections a number of times.

SMB is not an encrypted protocol as you have already found, so I strongly recommend against opening it to the outside world directly instead of allowing users to connect via a secure tunnel such as that provided by SSH or some form of more general VPN. I believe that the authentication method used is safe to perform in the plain (it is a challenge response arrangement that doesn't require plain text credentials to be transferred) so if you can guarantee that content on the shares is not sensitive you can get away with not using a tunnel/VPN but I would still recommend it as an additional level of security if only so that you can control who has access remotely separately from those who have access at all. Also a SSH tunnel or VPN can support compression which will reduce bandwidth requirements when the shares are accessed remotely.

There have been no successful unauthenticated remote attacks reported against Samba in my recent memory, so you are probably safe from that point of view, though again I'd suggest tunnelling the protocol instead of opening it plain. Having port 139 and others open will be an invitation to try if any remotely exploitable issues are found.

Another serious issue will be user password security. If the service is open and a user has an insecure password (either not complex enough, or something guessable by a cracker, and so on) then you have a serious problem. So you need to make sure you have a good password policy in place. Using a VPN like OpenVPN will mitigate this somewhat as people will need to have a keyset for the VPN too, though you can't guarantee that a user will keep their private key safe either...

Try checking port 445. That is the port for SMB over TCP in Server 2008.