Unable to Send Mail to a Specific Domain

I've searched the forum but found no answers.
I have a new iMac and a MacBook, both running 10.5.1
The email settings are identical on both computers (I checked many times over).
I can send an received mail on the MacBook, but can only receive email on the iMac.
Well - SOMETIMES, it will send email on the iMac. The majority of the time I get the message where I can select another outgoing email server (I have only 1) - I use the connection test, and everything shows OK. What gives??
UPDATE:
After some trial and error - I am finding that I cannot email to people with a certain domain. For example, My ISP is Cox.net (and so is my email) - and I cannot email to myself or anyone @cox.net. I can email out to people with Gmail email address though. I am confused even more now...
I have no one in my address book. Is it possible that some sort of corruption has occurred related to certain email addresses? If so, how would that be fixed?
ANOTHER UPDATE:
I found that if I select "remove from previous recipients list" for my own email address, I was able to send an email to myself.

On my MacBook (10.5.1) the port setting is in Preferences>Accounts>Advanced. It's grayed out on mine, why I don't know. I migrated settings from my iMac (running Tiger) when I bought it, and haven't tinkered with it at all. My settings also include password authentication. As I said, I've used it at a several airport lounges overseas, without any problems.

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