Different ports give me different errors. By that, I mean that according to http://mail.google.com/support/bin/answer.py?answer=13287 says to use either port 587 or 465. However I get different error messages for 465 vs. 587. I can't even tell which is closer to working, though it looks like 465 is better. Thoughts? 587's immediate error message: Sending failed: Your SMTP server does not support PLAIN. Choose a different authentication method. The server responded: "5.7.1 Credentials Rejected i20sm807304wxd" The message will stay in the 'outbox' folder until you either fix the problem (e.g. a broken address) or remove the message from the 'outbox' folder. The following transport protocol was used: wmeler@gmail.com 465's message (after literally minutes of working): Sending failed: Timeout on server smtp.gmail.com The message will stay in the 'outbox' folder until you either fix the problem (e.g. a broken address) or remove the message from the 'outbox' folder. The following transport protocol was used: tom.reagan@gmail.com In deciding to check port 465 vs. port 587, I tried the telnet trick Arun told me earlier. Alas, both seem to be okay from what I see in telnet: wmeler@linux:~> telnet smtp.gmail.com 587 Trying 64.233.185.109... Connected to smtp.gmail.com. Escape character is '^]'. 220 mx.gmail.com ESMTP 9sm616161wrl ^] telnet> quit Connection closed. wmeler@linux:~> telnet smtp.gmail.com 465 Trying 64.233.185.109... Connected to smtp.gmail.com. Escape character is '^]'. ^] telnet> quit Connection closed. Thoughts? (I am going to put together an email with all of my outgoing mail settings in a moment). Just hoping somebody knows something about one of those two error messages. -- Cheers, wmeler