Exchange 2010 Distribution List - External Emails

I have a new distribution list set up on Exchange 2010 with one "contact" added as a member.  That contact has an external email address.  When I send an email to that distribution list, nothing happens.  No NDR, no email outside, nothing.

Who is Participating?
Jon BrelieConnect With a Mentor System ArchitectCommented:
Not sure if exchange contacts burn CALs, but you can't add non-exchange objects to dist groups.  Well.. I mean, you can, but you'll have nothing to show for your efforts.

That info seems a bit outdated.  Note that step 3 says to "make sure create an exchange email address is checked."

Normally you can't do this from AD.  Maybe on SBS... Not sure.  

At any rate, this object must exist in exchange.  I don't think contact objects require CALs, but I'm no expert in licensing.
Jon BrelieSystem ArchitectCommented:
Does the Distribution List require that senders be authenticated?  That's the default in 2010.  If you're testing from outside the org, you need to un-check that.

Are you able to send email to the contact object directly?
bschwartingAuthor Commented:
Thanks for the idea.  I'm testing from inside, but I've removed that option as well just in case.  Still the same result.
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Jon BrelieSystem ArchitectCommented:
What about sending email directly to the contact?  Does that work?

If you put yourself into the distGroup, do you receive a copy of the message?
bschwartingAuthor Commented:
This is an AD "contact" and not a "user", so I'm not sure how I would email it directly.

I added myself to the dist group and received it successfully.
Jon BrelieSystem ArchitectCommented:
Oh... then you need to make it an exchange contact.  DistGroups can't send email to non-exchange objects.  
Recipient-Config->Mail Contact-> New Mail Contact.

Select existing, and browse to your AD contact. Complete the wizard.

 If you can't email it, Exchange can't either.
bschwartingAuthor Commented:
I was setting up as a "contact" with an email address hoping I wouldn't have to burn a CAL for exchange.  I was thinking this was possible as I've read about it on other sites.
Simon Butler (Sembee)ConsultantCommented:
Contacts don't use CALs, because they aren't accessing anything.
The key thing here is Message Tracking. See what Exchange has done with the message. It may well be that the message has been sent, but blocked as spam for some reason by the external recipient's email server.

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