UPDATE: Solved by configuring web server to use its own installed SSL cert, working fine on IMAP now Opinion: I think the SSL tools need improvement. I have tried SSL tools from other Mail Servers and were quicker to setup. Overall am satisfied with this mail server I just installed Smartermail and it seems to be working fine and all, but simply cannot get SSL to work. I already have a good working cert that I bought from Godaddy and worked fine on my previous mail servers. Keep in mind that I am NOT using IIS, am using a different web server so IIS doesn't apply here. I followed this tutorial here: http://www.smartertools.com/Portal/KB/a580/how-to-configure-ssl-tls-to-secure-smartermail.aspx?KBSearchID=246083 I am not sure how to use my existing cert, its a global domain cert and NOT a wildcard type cert? Any tips on importing existing cert? I only wish to use thi s with IMAP and would like to know how to test SSL on IMAP after cert is installed..