Error Sending Mail to Addresses Not In My Address Book

When trying to send a new email to anyone who IS in my address book, the outgoing mail sends successfully. However, when trying to send a new message to someone NOT in my address book, I get the pop-up window asking me which server to use. I click on the only server address I have set up and it immediately pops the same window right back up, won't send the message, and wants to place it into the outbox folder.
If I go into my address book and add the address I'm sending to, then go back and resend the mail, it goes through successfully.
I don't have this issue with my mail accounts on multiple other macs that we have. Why is the mail application on this one machine causing this annoying error?

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