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My old mans 2003 SBS Server is doing weird things.. specifically with Exchange. Inbound emails are trickling through slowly, but outbound emails have stopped working.

Is there a way to track outbound emails to see what is happening with them? We use a smart host which is our ISP.


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Try configuring Exchange to route email using DNS rather than the smarthost to rule the smarthost out as the problem. – joeqwerty Nov 15 '12 at 0:47
up vote 1 down vote accepted

Your first stop should be "Queues" under your server computer object in the Exchange System Manager. There should be a queue containing your outbound email in "Retry" state. Highlighting that queue should show you, under the "Additional queue information" frame, some reason why the queue is in "Retry" state.

You should definitely try to TELNET to the smart host's name, port 25, (telnet 25) from the server computer to see that you get an SMTP server banner. If you can't get that then message delivery isn't going to work.

Assuming that your server is able to reach the smart host's SMTP server you can use SMTP protocol logging to troubleshoot why your smart host isn't taking messages anymore. Personally, I'd sniff the traffic either with Wireshark or the built-in Network Monitor, rather than doing SMTP protocol logging, but that's just personal preference.

You will have success if you work to understand how the process should work and understand the protocol you'll have a much better time troubleshooting this.

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Thankyou. I worked it out, but accepted your answer as it was basically what I did to fix the issue. It appears my server was open to an authenticated relay attack. I've changed all passwords, cleared the queues (60,000 emails!!) and tightened up a few things and all is well so far. Thankyou! – Lock Nov 15 '12 at 21:55
Ahh, yes. Don't accept authenticated relaying from the Internet unless you really mean to do that. A good lesson. – Evan Anderson Nov 15 '12 at 22:01

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