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sending mail to distrubution list with external addresses will not forward to external address.

    Question

  •       Ok we have a user in our domain that wants all his email coming in to forward to both his secretary (internal email address) and to his gmail.com address.  We setup a distribution list that under his email account we set it to forward all email to his distribution list as well as send to his account.  This distrbution list contains his secretaries email address and and external contact we created for his gmail address.  We unchecked the "require that all senders are authenticated".  This allowed external people to send to distrubtion group.  Now we have his interal address and the secretaries address receiving the mail, but the external gmail account never receives the mail unless is comes from sombody internal. Thank you.
    Tuesday, October 11, 2011 12:05 AM

Answers

All replies

  • Check message tracking to see if the message is actually going out.
    If it is, then Gmail is probably blocking it as spoofed.

    Simon.


    Simon Butler, Exchange MVP
    Blog | Exchange Resources | In the UK? Hire Me.
    Tuesday, October 11, 2011 9:55 PM
  • Check Message tracking log a good suggestion.

     

    You can follow these to configure Message Tracking:

     

    Configure Message Tracking

    http://technet.microsoft.com/en-us/library/aa997984.aspx

     

    How to Configure Message Tracking

    http://technet.microsoft.com/en-us/library/aa997984(EXCHG.80).aspx

     

    If you use other accounts (eg: Hotmail or Gmail account )as the sender, send email to that user, will user’s Gmail get the email or not?

     

    Thanks,


    Evan

    Wednesday, October 12, 2011 9:27 AM
  •          Ok.  We looked at the message tracking log.  We picked a message that was sent as a test.  It doesn't seem to give a whole lot of information.  Here is the result of that message.

    Delivery Report for User ‎(user@email.com)‎

    Pending
    10/10/2011 4:38 PM server.domain.local
    Message was received by server.domain.local from cluster2.bresnan.net.

    10/10/2011 4:38 PM server.domain.local
    This message was redirected to another email address.

    10/10/2011 4:38 PM server.domain.local
    This message was redirected to another email address.

    Delivered
    10/10/2011 4:38 PM server.domain.local
    The message was successfully delivered.

     

    FYI, the message goes out just fine when we use the gmail.com address only in the forward address for his email.  It is only when we use the distribution group that it does not seem to work.  Actually it does partially work even with the distribution group because the email he receives from anyone on the domain makes it to the gmail.com address.  It is only email from external users that never makes it to the gmail account through the distribution group.

    Wednesday, October 12, 2011 3:24 PM
  • Do you have another message tracking log for the delivery of the message to the distribution group? That will show you what happens to the message when it hits the group for delivery to the external recipient. My instinct is that Google is seeing this has a spoof and is therefore dropping the message before it reaches the mailbox.

    Personally I discourage automatic forwarding with my clients for this very reason. With OWA being as rich as it is now, plus Outlook Anywhere, there is no need to have email go out to an external provider, where it becomes more difficult to keep track of message responses in the company name (rather than personal email address).

    Simon.


    Simon Butler, Exchange MVP
    Blog | Exchange Resources | In the UK? Hire Me.
    Thursday, October 13, 2011 6:49 AM
  •        Actaully we tried one of our addresses too and we have the same problem.  We have our own exchange server under our domain.  It seems to do it with any external email address. 

    Thursday, October 13, 2011 3:52 PM
  • Again - what does message tracking show? If it is occurring with any external address then something local is blocking it closer to home.

    Simon.


    Simon Butler, Exchange MVP
    Blog | Exchange Resources | In the UK? Hire Me.
    Thursday, October 13, 2011 10:22 PM
  •          Ok.  I am having trouble finding the way to check for the distribution group.  When I go to the message tracking in the Exchange manager toolbox area, I have a choice of mailbox to search.  So we pick the users mailbox.  The distribution list is not an option here.  An then you can search for messages to or from.  How would I search for message sent to or from the distribution group.  I guess this part is still unclear.  Or am I just plain not using the right tool? 

    Monday, October 17, 2011 11:38 PM
  • You need to use Message Tracking Log Explorer, which starts a tool, rather than the message tracking tool that starts a web page. You will also need to enter the distribution group's SMTP address as the recipient.

    Simon.


    Simon Butler, Exchange MVP
    Blog | Exchange Resources | In the UK? Hire Me.
    Tuesday, October 18, 2011 1:39 PM
  • Any luck resolving this issue?  I have the same problem just with a larger Distribution list, about 10 internal users and 20 external.  Exact same behavior though, I had thought exchange see's this a an attempt to relay mail and denies it.  But i can find no way to enable relaying for a DL as opposed to a connector.  Any body else barking up this tree?
    Thursday, December 15, 2011 9:35 PM
  • Its Simple.

    Just Create "New Mail Contact..." in "Mail Contact" in Exchange Server from the AD existing contact or new one and in this way you AD contacts got valid email in Exchange.

    Enjoy,

    John

    MCSA+Security

    Tuesday, March 26, 2013 12:35 AM