Sorry! I didn't get the email update on this post and didn't circle back because the client was making due with slow mailout put. I have checked on their system now and the Queue has all managed to go out. Thanks support and Doug for answering. Since you both provided some input, I've responded below

Support:
Setup is Direct
The Test emails within a couple Adagio modules in Email setup worked fine.
No recent updates, SSIMAIL.DLL is also 2.2.0.3 on this end
It was only erroring on sending items from the Queue.

Doug:
No Microsoft, Local ISP mail.tbaytel.net is the host in this case.