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Please open your email client and re-send the message from the sent messages folder." Was there something else I should have done while in telnet?I'm not sure what you meant by "try to push mail queue again" There are no other log entries matching the same ID -- just the two I provided. Sendmail should re-run queue every 30 minutes by default and re-attempt to send 'failed' messages every 30 minutes, then every 2 hours for 2 or 3 days until the message is either send or dropped.
I also tried disabling the symantec proxy and re-did the send using telnet, but nothing at all appeared in the log.Based on the above info, would you say that the problem is at the receiving end, or is there any reason to suggest something needs fixing at my end?Based on the above info, would you say that the problem is at the receiving end, or is there any reason to suggest something needs fixing at my end? Hardly it configured to keep message for 3 weeks in a queue.Each time the mail is 'deffered', there is a reason in log entry. I said about graylisting, because this reason was in your list and it's confusing if you don't know what is it.Why you can get 'operation timed out' - probably because remote server is either blocks your server in firewall or just not functioning.