Unfortunately no errors seem to appear,
I'm watching mail.log after performing a send/receive from Outlook while out of the office and with a message in my outbox.
I can see the connection from my IP to the mail server for courierpop3login (checking for new messages), but there's no other traffic listed between my IP and the mail server.
On the sending computer, Outlook simply stays with trying to send the message before finally failing and reporting back error code 0x80042109.
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