Going Mad: SMTP Problem

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I have certain emails that my mail program refuses to send, over and over again, saying it can't connect to my SMTP server. But other emails go out just fine -- and I only have one SMTP server in my list!

What the heck could be causing this?

UPDATE: Solved! I tried to add my university account to Apple mail, and it seems that the program sort of randomly sent certain mails from that account (so they didn't have my account / password info correct for Apple), while for most of my mail it used my Apple account. Once I noticed the different from address it was easy.

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