OK, now I'm getting a different error. The Windows machine seems to be finding the linux server as the message I'm now getting is the password is bad. Same password used to login to his Linux account.
Which pop server did you end up using? Some of them are designed to handle virtual sites so passwords are stored in a separate file. You also need to see if you can set the authentication method the client it using. Outlook, for instance, will prefer NTLM authentication, you need to use an auth method supported by the pop server.
I need some hints on how/where to look to see if POP is indeed coming up and what is going on between the two machines.
This sounds like a job for netcat to me. Netcat will connect you directly to any port TCP or UDP. Try:
nc server.example.com pop3
This should yield a message from your pop server saying what kind of server it is. You can then hit [ctrl]-[c] to break the connection, or play with the server if you know how to talk to it. A better way to terminate the connection would be to type QUIT and hit [enter]. The POP protcol is detailed here <http://www.ietf.org/rfc/rfc1939.txt>.
You may want to test it from the windows box. In that case you'll need the Win32 version of Netcat from <http://www.atstake.com/research/tools/network_utilities/> or directly <http://www.atstake.com/research/tools/nc11nt.zip>.
Netcat is incredibly useful for diagnosing network service problems. I'm thinking of implementing a simple webserver with netcat and expect (another incredibly useful tool).
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