I am pulling my hair out trying to figure out what happened to my mail server. I updated mysql from 5.0.88 to 5.5.6 and now I can't get my smtp to take my passwords. I can send mail if I login using webmail via squirrel mail. And I can get my email into my outlook but I can't send mail from outlook. I tried to use telnet to figure out what was happening. I set up my users password to test->encript in mysql tried the password every way possible under base64 test is dGVzdA== but it will not work.
535 5.7.0 Error: authentication failed: authentication failure
I used the following reference to setup the mail server http://www.howtoforge.com/virtual-users-domains-postfix-courier-mysql-squirrelmail-centos-4.8-i386
The only change was the version mySql. and everything works fine in webmail.