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Home Blog Geek Stuff Funky Microsoft Exchange problem - SOLVED!
Funky Microsoft Exchange problem - SOLVED!
Friday, 10 December 2010 12:32

Problem: For a single user, personal randomly gets external emails bounced back to her with the following NDR (sensitive data edited). This should never happen as the Exchange server uses a smarthost to send, so it should almost never create an NDR from itself...


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

Subject: xxxxxxxxxx

Sent: 12/10/2010 10:26 AM

The following recipient(s) cannot be reached:

' This e-mail address is being protected from spambots. You need JavaScript enabled to view it ' on 12/10/2010 10:26 AM

The message could not be delivered because the recipient's destination email system is unknown or invalid. Please check the address and try again, or contact your system administrator to verify connectivity to the email system of the recipient.

So the first step was to see where in the process the problem lies...so I went into Message tracking in Exchange (2003), and found the message, and that the address had "mailto:" attached to it. At first I kind of ignored that but the problem was staring me right in the face. The history showed the email being processed and an NDR being created, as expected.

Next, since we use a smarthost...Exchange shouldn't be using DNS and should just flat out send the email to the smarthost....so I was able to view a live log on the smarthost while the person attempted to send the email. Nothing showed up at all...which meant it was never getting to the smart host. Additionally I checked and sure enough DNS was working properly and resolved the domain.

Ok NOW what? I fire up Network Monitor to see if maybe Exchange is trying to contact the smart host at all. I do a capture while the person attempted the email, and look at the results. I see the email address show up in an LDAP query to active directory, meaning Exchange thinks the message is internal. I also notice the mailto: being attached to the address, which makes me double-back on that.

Went back to the user and looked at her sent item for that email. Go into the Outlook Properties for that recipient address, and sure enough it showed as email type MAILTO instead of smtp.

Had her redo EXACTLY step-by-step to what she did. She mentioned she did copy and paste the maito: address but removed the mailto: portion from the address bar. While we were talking, (before removing the mailto), Outlook accepted the address and changed the address to only show the actual email address. I went into the Outlook properties, and sure enough email type was MAILTO.

So...in the end, we figured out she started to type in the body of the email first, was going to go back and remove the mailto before sending...Outlook changes it 10 seconds in and shows just the email addy, user thinks its ok and sends.

Fix: Have user copy and paste just the address OR remove the mailto: portion first.