SMTP AUTH with SSL via Mail clients fail. Successful using command line. Successful without SSL. Ubuntu 10.04, Postfix, Dovecot, squirrelmail stack

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http://serverfault.com – I have set up an email server stack with Postfix, Dovecot and SquirrelMail. Everything works except SSL communication with the SMTP server. When I manually test the communication by following the instructions here: http://qmail.jms1.net/test-auth.shtml I am able to connect and send email no problem. My main email client is Mac Mail but I have also briefly tried Thunderbird and it failed as well. I have been struggling with this issue for days to no avail so any help would be greatly appreciated. I have attached the verbose server logs as well as the logs from my mac mail client Server l (HowTos)