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User not receiving non-delivery reports in Exchange Server 2003

After sending email that doesn't get delivered, an Exchange Server 2003 user is not receiving non-delivery reports, but why?

Q: A user on our network sent an email from her home account. According to our Exchange 2003 server, the email never gets delivered, then a non-delivery report (NDR) is sent. The user never receives these NDR notifications. Do you have any idea what the problem could be?

A: There are a number of factors that could cause this behavior. Your first measure should be to find out what sits between your Exchange server and the user's home account. Specifically, are there any antispam gateways in between? Usually in cases like this, an antispam gateway is catching and quarantining the NDRs or they are ending up in the user's Junk mail folder. You may also want to check if the user has any other rules set on their mailbox. I've seen many cases where rules can fire in unexpected circumstances and cause similar behavior.

If you think it may be something on your end, you should try sending messages from outside your organization to a mailbox with a delivery receipt on them (or try sending to a non-existent address in your domain) to observe what happens on both sides. This gives you a controlled setting where you can carefully examine both sides of the equation to isolate the issue and to confirm that NDRs are truly leaving your environment.

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