Check it out in the morning. On when it will be fixed. The ssl is ugly, I know.

As to the cert issue and thunderbird, its seeing your ssl cert as self signed which is why it is asking you to allow its use. See,browsers can do look ups on a ssl cert to get the chain since they already have some of the information. On the mail clients I think this needs to be pushed over. Any way, how to will get you working with exception of ssl ( i know ).

So, you can accept the cert in thunderbird and all should be fine, just gonna be thinking its is using a self signed cert.

If webmail ( roundcube ) is the only thing that is not working ( telnet does yeah? ) , then check its logs. Thats what I would do.

Alright thanks for further helping me once again. I will try and read the logs, im assuming they are located in the directory where I put it in (/var/html/roundcube). If not I will just google.

EDIT: Alright so I found the log, it said it did not support some type of authentication. I found this guide https://bbs.archlinux.org/viewtopic.php?pid=877180 and was told to remove %u in smtp_username and %p in stmp_password in the roundcube main.php config file and I can now send mail to myself and other emails addresses, however I can't receive mail from other mail servers (except for myself), I believe this is because my domain inst registered yet. I have a few concerns though, I AM almost certain postfix/dovecot is using SASL Authentication because when I didn't have it enabled I could only send emails to my own domain and now I can send it to other domains. However, how would I get roundcube to encrypt the login data or is that part of what SASL auth.?

P.S. I know I am not 100% done with my mail server, I still need spam filters (dkim with clamav?).