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I am able to send email to individual users but when not when they are in a distribution group. When I do I get this report.

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. #5.3.1

However, like I said before I can select their name from the GAL and send mail that way. Their email address is exactly the same in both the GAL and distribution group. The only difference is these users have external email addresses.

Windows Server 2003 Exchange Server 2003 Outlook 2007 and 2010.

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2 Answers 2

Well, One work-around is removing the problematic users from the group, adding them to their own distribution group and nesting the new group in the original group.

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The message could not be delivered because the recipient's destination email system is unknown or invalid.

...

The only difference is these users have external email addresses.

Uh, there's your answer.

Your mailserver is trying to deliver to the external email address, rather than the internal one, and it can't find the system that serves the external email for your domain (possibly because it doesn't know to look at itself). I'd look into correcting that underlying issue, rather than just segregating the users with external email addresses into some nested group.

Strikes me as a reminder of why all email addresses should be external, but that's probably a topic for a different question.

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I find it strange that It didn't have this issue before and why its able to send when in one group and and not in another. Thanks for your answer. –  Jake Aug 29 '12 at 7:13

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