I connected to a Windows Server 2008 R2 shared folder from a Mac OS X Mountain Lion computer over the Internet using this command:
mount -t smbfs //user@server/path/to/share local_folder
Is traffic encrypted by default? What settings do I look at (if any) to know whether it was encrypted? If it wasn't encrypted, what's the easiest way to encrypt it? Was the password I typed at the command line encrypted?
Update: sysadmin1138 has addressed the password question. Does anyone know how I can tell if the traffic itself is being encrypted?
Best Answer
It is encrypted, Windows doesn't ever transmit passwords in the clear, but the question you should be asking is how well it is encrypted. That's up to the Windows server and the OSX install to negotiate. The Samba that comes with OSX is smart enough to use NTLMv2, so chances are it had fairly good encryption. But...
How long was the password? If the password is anything shorter than 15 characters it is a lot easier to brute-force decrypt than one longer then that threshold. And gets a lot easier for each character under 15. Weird character-sets will help of course, but 'keyboard-typable' is increasingly easy to retrieve.