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I have a user that sent an email to 6 people. 3 of them were external addresses, and 3 were internal. The 3 internal users all got theirs, but the sender still got a return.

Typically, at the bottom of the return you get this message:

Your message did not reach some or all of the intended recipients.

   Subject:    <insert subject here>

   Sent: 7/27/2010 10:39 AM

The following recipient(s) cannot be reached:

However, there isn't a list of recipients and failure reasons, the email simply ends. How can I go about finding out which addresses failed? I've checked event logs on the Exchange server, with nothing of relevance in there.

This is Exchange 2007 Enterprise on Server 2003

EDIT1: I've already been through the Message Tracking utility. The parameters selected were Sender, EventID = Fail, and todays date. It shows no messages failed.

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2 Answers 2

up vote 1 down vote accepted

The "Message Tracking" functionality in Exchange is going to be of the most assistance to you here. Searching the message tracking logs will tell you more about attempted deliveries and the outcome of each attempt.

If you can't get enough detail from message tracking, however, you might want to consider using SMTP protocol logging or even sniffing the traffic between the Exchange Server computer and the recipient's email server if you really want detailed analysis.

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See Edit1 –  DanBig Jul 27 '10 at 15:17
    
The only thing I see thats odd, is a particular result list. It shows only 2 of the external recipients in the field, so I'm assuming the missing one is the problem? They are all to the same external domain, btw. –  DanBig Jul 27 '10 at 15:21

Since it's a small number of external addresses you have to check, I would telnet to the individual servers and test the smtp connectivity to those addresses as outlined by MSFT here. Do an NSLookup of the mail servers for the domain and see if you can reach them. Send a test email to the same addresses as your user did and see what happens. Shouldn't take more than 10 minutes and you can find out real quick if it reproducible.

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The 3 external recipients were all on the same server. We have been able to send to them as recently as yesterday. It also appears that only 1 of them failed, just looking for the reason why. –  DanBig Jul 27 '10 at 15:53
    
@Dan, it may be that it's not you, and something changed on their end. I would still try the telnet approach, and send as an email address that you can check, so you can see which one bounces back. If you do it individually instead of all three at once, you can localize the problematic email address on their end. –  Holocryptic Jul 27 '10 at 16:03
    
I don't believe that he'll get a bounce back from a message sent via a telnet session, but if he tests each email address individually as you suggested, the SMTP telnet session should indicate which recipient email address is having the problem. –  joeqwerty Jul 27 '10 at 16:28
    
@joeqwerty, in the telnet session you can specify who the mail is coming from (MAIL FROM:Admin@test.com). Any bounce backs should come back to this email address, shouldn't it? –  Holocryptic Jul 27 '10 at 17:15
    
I know about the Mail From: command but I'm just not sure that sending an email via a telnet session will generate a bounce back on an invalid recipient. I've used telnet a lot to test email and don't remember ever getting a bounce back. On the other hand, if the recipient is invalid (mailbox full, no such user, etc.) the server will let you know it in the telnet session via an SMTP status code (550, etc.). –  joeqwerty Jul 27 '10 at 18:20

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