Google Apps and Exchange Distribution Lists

Posted on 2012-08-23
Last Modified: 2012-11-02
Hi all,

I'm in the process of testing Google Apps for our company. We only want around 10 people to have Google Apps in the beginning so we have split delivery setup. It goes a bit like this:

Email ¿ -> Google's Servers -> Google Apps users -> Gmail inbox
                                                  | <- Non Google Apps Users
            Exchange Server

So far there are only two accounts setup in Google Apps. They were both address' that existed on the exchange server before. The mailboxes have since been deleted.

To get the exchange server to send internal mail to the Google apps users I had to add "" to the "Forward all mail with unresolved recipients to host" setting.

Everything seems to be working OK with that setup Google Apps users get their email no problem and the exchange users email is unaffected.

Exchange users can also send email to Google users.

However the problem comes when I try send email to my Google users after I have added them to  distribution groups.

I though the easiest way to do this was to make a contact in active directory and set the email alias to an SMTP address: Then I added this contact to a group:

The delivery fails, every time.

I get this:

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

      Subject:  Test 
      Sent:     22/08/12 12:00

The following recipient(s) could not be reached:

      User Google Apps on 22/08/12 12:00
            A configuration error in the e-mail system caused the message to bounce between two servers or to be forwarded between two recipients.  Contact your administrator.

            < #5.4.6>

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This persists until I remove the contact from active directory.

Google Apps is pretty useless to me unless I can add my users to distribution groups.

What's the problem here? Can anyone point me in the right direction?

Thanks for any help.
Question by:IT_anglo
    LVL 16

    Expert Comment

    Your example is a bit vague, but if I had to guess I would say that you need your DL contact member to point to

    Author Comment

    Sorry I should explain a bit more:
    We have Exchange 2003.

    The MX records point to Googles servers, all email for our domain is sent there.

    Any Email alias' matching Gmail users are kept on Google's servers where Google Apps users can access their email.

    All other email is routed to the The MX records for that sub-domain point to which directs email to our exchange server.

    I tried as you suggested but I didn't get a NDR or an email.

    Is there any more information I could provide that would be helpful?
    LVL 18

    Assisted Solution

    Your question is little bit confusing.

    Let me confirm this:

    Your domain email is had pointed to Google server. Your Exchange email domain is, your exchange user will have an email address as while user at Google will have If this statement is true, then you may have 2 MX records.

    1. MX = pointing to Google server
    2. MX = pointing to your Exchange server

    I though the easiest way to do this was to make a contact in active directory and set the email alias to an SMTP address: Then I added this contact to a group:

    Based on your statement and if my statement is correct, your group (Exchange) will have email address as NOT You have to create a mail contact as and added to
    LVL 63

    Assisted Solution

    by:Simon Butler (Sembee)
    The problem here is that you are trying to use the same domain in both locations.
    By creating a Contact in the domain with that address on it, which also matches the lcoal domain you have basically confused Exchange.

    The only option is to have a second domain that you can use to forward the email out. This second domain can go on to the same contact, so that user @ and user @ are both on the contact. As long as user @ is the DEFAULT address on the contact, then Exchange will send the email out to the external address.

    There is no other way that you can have non-Exchange users on an internal list. Remember Exchange expects to be responsible for all email for a domain.

    LVL 1

    Accepted Solution

    For all users that are on Google, you need to setup Dual delivery. Google has a built in Alias that is added to every user see below:

    A plan of the mailflow required is found here -

    To setup forwarding for your users instructions are found here -

    Every Google User needs to have a contact that points to their Google alias as above.

    Hope this helps

    Author Closing Comment

    Apologies for delay in allocating points, a colleague left this open! Thanks for your help.

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