Random Sending - Mail.app

RyanA

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I'm using mail with three IMAP accounts, all of which are using the same SMTP account. It's my own mail server, so I know this works.

My problem is that randomly, messages will not send. I'll resend, and resend, and eventually they will go, but I have not been able to generate a repeatable reason why they actually send. There's no rhyme or reason to this, and I have never had this problem before in any other software. Any ideas?
 
Hmmm...what does the activity viewer in the mail app say?
Any logfiles?
What's the mail server running? (God, don't let it be Exchange!)
 
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