@Carl, Yes, I do know that even 2 successive tries with the same command can be different, even without an IP Address change. What is of note is that the first attempt going through the router...

@Carl , I have some more data, TRACERT acts strangely. Could be part of the problem? I did some TRACERT's to the different e-mail servers... very strange and and maybe the reason it isn't working? I...

Carl wrote @IrvSp Oh i understand, incoming and outgoing are different protocols and ports but it does appear that there is something blocking the outgoing service on the router. Epically since its...

@Carl Thanks, I'll post back here what happens with the TeamViewer session as well. It just boggles my mind how I can GET e-mail from the same server, but can NOT send e-mail via the same server....

@Carl I don't think it is a service? Note even a PORT as my mail server when on the network can use 3 different one. General SMTP port settings for CHARTER.NET Outgoing (SMTP) Secure - Port: 465 for...

@Carl Just put the A20 back and I still have the problem... clearly in the router somehow? Do you think this is a Trend Micro how would I contact them? I thought I saw another post somewhere here...