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Proposed AnswerEmail management with a secondary mailbox

  • Friday, October 30, 2009 10:33 AMCommacom Users MedalsUsers MedalsUsers MedalsUsers MedalsUsers Medals
     
    Hi

    I have a problem in Exchange 2007 on SBS 2008 which is causing a bit of head-scratching.

    The particualrindividual needs, for admin purposes to have all his inbound mail copied to another address on another domain. This was easy to setup by creating a contact and then setting that contact as a forwarding point in the delivery options within mailflow settings in Exchange Management.

    The sting in the tail is that while this works fine for ordinary inbound messages, when the message is in reply to an outbound message then the reply is only received by the remote account and not in the persons Exchange mailbox.

    This strategy worked perfectly in SBS 2003 but seems to be another SBS2008 process which does not behave in the same manner as the older versions.

    I would appreciate hearing about a simple method to make this work.

    Many thanks

    Neil

    PS I had a look at setting this as a rule in the Outlook client, but that too seemed to be a little problematic when the PC is switched off.

All Replies

  • Friday, October 30, 2009 12:31 PMAndyD_MVPUsers MedalsUsers MedalsUsers MedalsUsers MedalsUsers Medals
     
    Which account is sending the outbound message?
  • Friday, October 30, 2009 12:34 PMCommacom Users MedalsUsers MedalsUsers MedalsUsers MedalsUsers Medals
     
    The original sender is the user on the domain. The original recipient is external, e.g. a gmail account, and another domain account as tests.

    External replies seem to fall foul of this but not internal ones.

    Neil
  • Friday, October 30, 2009 12:38 PMAndyD_MVPUsers MedalsUsers MedalsUsers MedalsUsers MedalsUsers Medals
     

    And the Default reply is set to the internal SMTP domain you are authorative for?

    Im trying to understand how the replies fit into this, because it sounds as if the external user is replying back to the SMTP address of the remote account.

  • Friday, October 30, 2009 1:00 PMCommacom Users MedalsUsers MedalsUsers MedalsUsers MedalsUsers Medals
     
    In all the test messages I have sent the reply-to is the normal email address of the domain user.

    The message headers do not have anything in them that suggests to me that the message should be differently handled.

    It seems to me that it is the threading of the message which is leading to the problem, if that makes sense, as a 'Re:' message, sent as a copy, to the user is treated in the 'original message' way and received in both locations.

    The more I thinks about this the more puzzled I become.

    Sadly the current secondary destination does not permit access to the message headers of the problem messages. All we can acces are thos of the original, conversation initiating message.

    Neil
  • Saturday, October 31, 2009 1:09 AMAndyD_MVPUsers MedalsUsers MedalsUsers MedalsUsers MedalsUsers Medals
     

    Yea, from here its hard to see how this is happening. What if you created a hub transport rule instead that copied all inbound messages to that other external account and you removed the forwarding on the account and tested?

  • Sunday, November 01, 2009 5:02 AMSachin BP Shetty, MCITP Users MedalsUsers MedalsUsers MedalsUsers MedalsUsers Medals
     Proposed Answer
    Neil,

    Please follow the instructions from the below MS Technet library.

    http://technet.microsoft.com/en-us/library/bb124314%28EXCHG.65%29.aspx
    Have a good day, Sachin Shetty| MCP|MCTS|MCITP-EMA|
    • Proposed As Answer byRajesh9189 Sunday, November 01, 2009 6:31 AM
    •  
  • Sunday, November 01, 2009 1:54 PMAndyD_MVPUsers MedalsUsers MedalsUsers MedalsUsers MedalsUsers Medals
     
    Neil,

    Please follow the instructions from the below MS Technet library.

    http://technet.microsoft.com/en-us/library/bb124314%28EXCHG.65%29.aspx
    Have a good day, Sachin Shetty| MCP|MCTS|MCITP-EMA|

    I dont see how an article about resource mailboxes is relevant for this issue.
  • Monday, November 02, 2009 4:22 AMRich Matheisen [MVP] Users MedalsUsers MedalsUsers MedalsUsers MedalsUsers Medals
     
    On Fri, 30-Oct-09 12:31:18 GMT, Andy David wrote:

    >Which account is sending the outbound message?

    It sounds like the remoe system is sending the reply to the address in
    the Return-Path.

    When the message is sent to an alternate recipient Exchange inserts
    the "Resent-*" header and the message is sent with the MAIL FROM
    address being the one assigned as the primary SMTP proxy on the
    Contact (or the mail-enabled user or distribution list if those are
    nominated as alternate recipients).

    sage remains the same, but the recipient
    may see the message as "Sent on Behalf Of".
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP

    --- Rich Matheisen MCSE+I, Exchange MVP
  • Tuesday, November 03, 2009 4:18 PMCommacom2 Users MedalsUsers MedalsUsers MedalsUsers MedalsUsers Medals
     
    Hi Rich

    I am afraid I cannot see that as the problem.

    In the test cases, for example to a gmail account, the message is sent from the PC by Outlook to my gmail account. (sencondary address not relevant here)

    At gmail I reply to the domain email address. The message must be being received by the exchange server as it is only from there that the alternate is connected with the address of the domain user. The reply does not, however reach that user, but gets bounced out to the alias only.

    When the alias was created as a contact and added to the delivery options, the option to have messages delivered to BOTH accounts was selected, but does not appear to be actioned. Why this is only for replies is what is causing the hair-tearing this end.

    When I look at the address being replied to it is ONLY the domain user's address and not the secondary, indeed the secondary address appears nowhere in the headers. This, again, points to a mis-handling of the deliverty option. What I need to find is a way to correct what is beginning to look like a bug.

    Neil
  • Wednesday, November 04, 2009 4:15 AMRich Matheisen [MVP] Users MedalsUsers MedalsUsers MedalsUsers MedalsUsers Medals
     
    On Tue, 3-Nov-09 16:18:12 GMT, Commacom2 wrote:

    only.When the alias was created as a contact and added to the delivery options, the option to have messages delivered to BOTH accounts was selected, but does not appear to be actioned. Why this is only for replies is what is causing the hair-tearing this end.When I look at the address being replied to it is ONLY the domain user's address and not the secondary, indeed the secondary address appears nowhere in the headers. This, again, points to a mis-handling of the deliverty option. What I need to find is a way
    >to correct what is beginning to look like a bug.Neil

    How about looking at the SMTP receive logs to see what RCPT TO
    addresses were in the transaction? If the one assigned to the mailbox
    is there then the message should be bifurcated and both the Contact
    and Mailbox should receive the message.

    If there's another address in the RCPT TO command that would be
    telling.

    Never trust the contents of the message when trying to decipher SMTP
    mail flow. You'll drive yourself nuts.
    ---
    isen
    MCSE+I, Exchange MVP

    --- Rich Matheisen MCSE+I, Exchange MVP