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exchange 2003 email enabled contact

I have MS Exchange 2003 & have set up a mail-enabled contact in Active Directory for a user who wishes to forward email to an outside email address.  When email is sent to that user from inside the organization, it is delivered to the outside email address.  When email is sent to that user from outside of the organization, it is never delivered & the sender gets an undeliverable notification (with a status of 5.7.1).  I have created additional email-enabled contacts & tested with those & they all behave the same way.
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BHR
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BHR
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1 Solution
 
strivoliCommented:
Check Contact's properties in AD and allow "Receive messages from anyone".
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BHRAuthor Commented:
It was already checked (by default).
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strivoliCommented:
Is the Contact's domain different from other (working) Contacts?
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strivoliCommented:
Furthermore, in AD check the option "Only Authenticated Users" isn't checked.
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BHRAuthor Commented:
I haven't been able to get any email-enabled contact to work correctly (regardless of their domain).
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BHRAuthor Commented:
Nope, that isn't checked (again by default).
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strivoliCommented:
OK. Sorry. I understood that others contact are working. I misunderstood.

Which is the domain of the normal users (not contacts)? Is it the same domain of the contact? If it isn't did you set MX record for Contact's domain in order to get the mail from outside?
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BHRAuthor Commented:
The domain of the normal users is the domain of our organization.  This is not the same as the domain of the contact (which is the user's personal email).

I don't understand why I'd need to set up an MX record for an outside domain.  

Let me just give an example of what I'm trying to do.  A contracted employee John Smith has a personal email (say johnsmith@gmail.com) account that he wants to use exclusively for all of his correspondence.  Instead of creating a user account in active directory for him (since he would never actually be in the office to log into a company computer or use a company email address, say johnsmith@company.com), I just want to set up an email-enabled contact with his personal email address.  That way I can include this address in a couple of company (active directory) distribution groups.
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strivoliCommented:
You wrote "When email is sent to that user from outside of the organization, it is never delivered" and that makes me think of this example: I send a mail (I'm outside of the organization) to johnsmith@gmail.com using your server and that mail fails.
If my example (above) is not your scenario, please make an example in order to understand what's your scenario.
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BHRAuthor Commented:
If you sent an email from an outside email domain to a email-enabled company distribution group with an email address of group1@mycompany.com (which the email-enabled contact of johnsmith@gmail.com is part of) it would go to the other members of the group who have a "@mycompany.com" address but would not go to John Smith at his outside email address.  

If I sent an email from within the organization, it would go to all members of the group including johnsmith@gmail.com.
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Simon Butler (Sembee)ConsultantCommented:
What is the exact text on the NDR? The code on its own is not enough.

The way that Exchange forwards email makes it look like your server is spoofing the ORIGINAL sender of the message. If the recipient is using spoof filtering then the message could get rejected.

Simon.
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BHRAuthor Commented:
The message that the end user recieves is:

     This is an automatically generated Delivery Status Notification.

     Delivery to the following recipients failed.

     johnsmith@gmail.com


and the error attached to the email is:

     Reporting-MTA: dns;mail.mycompany.com
     Received-From-MTA: dns;barracuda.mycompany.com
     Arrival-Date: Fri, 14 Jun 2013 11:06:02 -0500

     Final-Recipient: rfc822;johnsmith@gmail.com
     Action: failed
     Status: 5.7.1
     X-Display-Name: John's Account


(the address & domain have been changed to fit the example)
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Simon Butler (Sembee)ConsultantCommented:
Gmail uses antispoofing technology (Google are one of the major players in this field). Therefore if it is a Gmail account that is the target, then what you want to do is not going to work 100% of the time.

Are you using a Barracuda? If so that is probably blocking the message as well, for the very same reason.

Bottom line is that having external contacts as a forward on a mailbox will usually have failures, the rate of failure depending on the target and the source. I actaully don't allow external contacts for forwarding on the environments that I support for that very reason.

With smart phones and OWA, forwarding email to an external address can be avoided with the user accessing their email another way.

Simon.
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BHRAuthor Commented:
I don't think it is the Barracuda, as that would only block incoming emails & the incoming emails to the group is coming in fine.  It is only the forwarding/outgoing to the gmail account that isn't working.

OWA & mobile access to company.com emails aren't an option, as this user will only use his personal email account.  

Looks like I will have to create an active directory user/email account for him & setup the forwarding using Outlook rules.  Not really the way I wanted to do it as it uses up a CAL, but if that is the only way it'll work I have no choice.
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BHRAuthor Commented:
Your comment about Gmail using antispoofing tech helped me decide not to spend too much more time on this, but to just set up the forwarding using Outlook.
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