How to dissect raw data in an email

Question

There may be an obvious answer to this question, but I have not found it yet. I have two email messages that were sent to two different people in our company. One individual did receive the message, the other did not. I want to try to better understand why. One way that I can think of to do this is to pick apart the raw email message (we use Exchange 2003) and see if there is a possibility that the problem resides at the senders side rather than our side.

What techniques are typically use to dissect email messages and/or verify their validity. Also, what can be done on the Exchange side to understand what may have happened to undelivered email messages. I have asked our local exchange administrator, and he can't answer the question for me, so I'm looking to the community for help -- Thanks.

Answer 1

You can use Exchange's message tracking feature to see exactly what path the incoming messages took; that's where I'd start. There's a decent tutorial here. Note that this is something your Exchange admin will have to do.

Answer 2

Well I don't think it's possible do dissect an email message that never arrived :)

1) You should eventually receive an NDR at the sender indicating why a message failed.

2) Enable Message Tracking and you'll get a log of all the messages through the server. Here's a little walk-through .

3) Enable logging in the SMTP service (if the messages originated outside of the server).

4) Check your firewall logs, especially if they do any sort of mail filtering (many do).