How to Test SMTP AUTH using Telnet
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:
website to help with conversion: http://www.hcidata.info/base64.htm
@ symbol was messing with perl
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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:
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telnet mailserver.com 25 | 
Greet the mail server:
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EHLO mailserver.com | 
Tell the server you want to authenticate with it:
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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:
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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:
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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:
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user@localhost [~]# telnet exampledomain.com 25Trying 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 +0200220-We do not authorize the use of this system to transport unsolicited,220 and/or bulk e-mail.EHLO exampledomain.com250-server1.exampledomain.com Hello  [1.1.1.2]250-SIZE 52428800250-PIPELINING250-AUTH PLAIN LOGIN250-STARTTLS250 HELPAUTH LOGIN334 VXNlcm5hbWU6dXNlcm5hbWUuY29t334 UGFzc3dvcmQ6bXlwYXNzd29yZA==235 Authentication succeeded |