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Thank you in advance for your patience and understanding on the matter.
Figured it out with the help of Plesk tech support. I was on an older version of PHP which was not as strict when it came to SSL certificates so the mailing scripts were written prior to PHP 5.5 and the host connection mail.mydomain.com did not have a certificate issued only a certificate to mydomain.com adding the certificate to mail.mydomain.com fixed the issue.
Thanks for everyone's help