I’m not sure what’s going on or where to look but it seems that mail is either taking forever to send or not at all anymore.
Have a look in /var/logs/mail.log.
It is also possible to get more log detail … in /etc/postfix/master.cf find these lines and add the -v to the end, then do sudo postfix reload.
smtp inet n - y - - smtpd -v submission inet n - - - - smtpd -v
(This logs a lot more detail. Multiple -v options make the software increasingly verbose, start with just one -v. You probably want to remove the -v’s when you’ve sorted things out.)
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I think a lot of how I’m using this is likely my fault in this case I’m going to consider this closed for now. That log file tells me a lot of useful stuff I wish I had it earlier.
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