I got the certificate issue resolved. It seems I needed to combine the certificate and the chain bundle into one file.
I also got the blocking issue resolved.
Now it seems the PBX is sending out the email as user asterisk and not the email server account setup in /etc/postfix/sasl_passwd
It would seem to me the System Admin Pro should be taking care of all at. I think will see what support has to say before start making changes as on the setup section it says:
On this page you can set your SMTP Server information to receive e-mail notification and voicemail to e-mail.
Please note that due to the security settings of some mail servers (1and1, GMail), you may need to manually configure additional settings.
Because it’s a bug and it probably hasn’t been reported properly until now. This hasn’t worked for at least the last 6 months as I’ve had to make changes to support the Office 365 updates in the recent months. It required all this to be done because System Admin Pro wasn’t doing it.