Below are instructions on how to test SMTP AUTH against a mail server using Telnet and entering the commands by hand.
The first thing you need to do is get a base64 encoding of your username and password. There are a couple ways to do this, the example below uses Perl:
perl -MMIME::Base64 -e 'print encode_base64("username");' perl -MMIME::Base64 -e 'print encode_base64("password");'
What will be returned from each command is a base64 encoding of the username and password; save these as you will need them later. Now connect to the mail server using Telnet:
telnet mailserver.com 25
Greet the mail server:
EHLO mailserver.com
Tell the server you want to authenticate with it:
AUTH LOGIN
The server should have returned 334 VXNlcm5hbWU6; this is a base64 encoded string asking you for your username, paste the base64 encoded username you created earlier, example:
dXNlcm5hbWUuY29t
Now the server should have returned 334 UGFzc3dvcmQ6;. Again this is a base64 encoded string now asking for your password, paste the base64 encoded password you created, example:
bXlwYXNzd29yZA==
Now you should have received a message telling you that you successfully authenticated. If it failed your user/pass may have been wrong or your mailserver is broken.
Below is a log of a real successful SMTP AUTH connection over Telnet:
user@localhost [~]# telnet exampledomain.com 25 Trying 1.1.1.1... Connected to exampledomain.com (1.1.1.1). Escape character is '^]'. 220-server1.exampledomain.com ESMTP Exim 4.66 #1 Wed, 09 May 2007 23:55:12 +0200 220-We do not authorize the use of this system to transport unsolicited, 220 and/or bulk e-mail. EHLO exampledomain.com 250-server1.exampledomain.com Hello [1.1.1.2] 250-SIZE 52428800 250-PIPELINING 250-AUTH PLAIN LOGIN 250-STARTTLS 250 HELP AUTH LOGIN 334 VXNlcm5hbWU6 dXNlcm5hbWUuY29t 334 UGFzc3dvcmQ6 bXlwYXNzd29yZA== 235 Authentication succeeded