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This problem really bothered me too. (Time Warner: kc.rr.com) I could send email via wifi or when connected to ActiveSync. But when I could not get it to go otherwise. I found the solution on the ATT user forum.
The solution: Use cwmx.com as your outgoing (SMTP) server. I do have "Outgoing server requires authorization" and "Use the same user name..." both checked.
Now, one note: I got this to work using the built-in Messaging but not Flexmail. So far, I have not had the time to research it on Webis's forums or support.
Hope this helps!
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