Exchange - Internal to External Routing Issue for abc.local and

Discussion in 'Windows Small Business Server' started by Kev, May 3, 2006.

  1. Kev

    Kev Guest


    I have a problem with internal to external mail routing, this is a
    temporary issue as I am having a fixed IP arranged and then will host
    all mail in house. Before SBS was installed all the office users
    employed POP through Outlook, and the users in field a webmail
    interface at the ISP.

    Setup is SBS 2003 Premium, ISA 2004 installed. ISP provides Dynamic IP
    at the moment and hosts the public domain name, The internal
    domain is abc.local. The CEICW has been run to use DNS for the domain Each user has a well known email address with a format:
    - so an address of this format has been added to
    each uses email address and set as the primary so it is used in the
    from field.

    Mail is picked up by users in the office via POP through Outlook and
    users working in the field pick up mail via webmail from the ISP; I
    know that I could use the POP connector but the office users have
    multiple POP accounts (with the same ISP) some of which need to have
    the messages left on the server for a period. I do not believe that I
    have that option with the POP connector.

    If one office user sends a message to ,who in fact works
    in the field and picks up mail via webmail, of course Exchange routes
    it internally and if there is no "john" in the directory returns a

    I thought that perhaps running the CEICW and using abc.local as the
    email domain name might fix it, all mail for being routed by
    DNS and picked up by the ISP. This didn't help and in fact no mail to was deliverable.

    Does anyone have any thoughts on how with an internal domain of
    abc.local and a public domain of I can configure
    Exchange/Outlook to deliver all mail for to the ISP? Then all
    internal users will get the message when they collect their POP mail
    and all users in the field will get it via webmail.

    Thanks for any thoughts.
    Kev, May 3, 2006
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  2. Hi,
    If I understood your issue correctly, the following KB seems to cover a
    similar scenario of a 'shared' email domain namespace.
    The KB is aimed at customer using the POP3 Connector, but the
    resolutions/workarounds should be the same.

    300681 E-mail to external recipients with the same e-mail domain causes NDR
    messages when using the POP3 Connector;EN-US;300681


    Damian N. Leibaschoff, MS IST, MCSE
    Microsoft Corporation

    Get Secure! -


    When responding to posts, please "Reply to Group" via

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    This posting is provided "AS IS" with no warranties, and confers no rights.

    Damian N Leibaschoff [MSFT], May 3, 2006
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  3. Kev

    Kev Guest

    Thanks Damian,

    I will study the KB article.

    Kev, May 3, 2006
  4. Kev

    Kev Guest

    Hi Damian,

    I followed the instructions in method 2 of the KB article, modifying
    the deafult recipient policy and adding a new one.

    However, say for a user "tony" who has:

    The last address being set as the principal address on the Email
    Addresses tab, as this company uses as the SMTP
    naming scheme.

    Now this user works mainly in the field and picks up his mail from the
    ISP's POP server.

    Internally I have tested the set up and when Tony Smith is selected
    from the address book the message goes to his Inbox and when
    is typed into the To: field the message also goes to his

    The Exchange server is not authoratative for but as
    is an address in his profile the message remains
    internal. The objective is to allow "tony" to work in the field and
    for uses in the office to mail him at so that he can pick
    this mail from the POP server.

    Am I missing a piece in the configuration? Any further assistance
    would be great.

    Kev, May 4, 2006
  5. Hi Kev,

    Why not have Tony pick up his email from the SBS (Exchange), instead of the
    ISP? There are many advantages, including full access to his mailbox which
    includes tasks, calendars, reminders, contacts, etc. And he always knows
    where his mail is, and it's always in one spot.

    He can use Outlook Web Access (dead simple), Outlook over the Internet
    (RPC/HTTP), or even IMAP or POP. Your Exchange server can do all these

    Does Tony have a latptop, or other mobile device that he genarally always
    takes with him when he works away from the office?
    Les Connor [SBS Community Member - SBS MVP], May 4, 2006
  6. Kev

    Kev Guest

    Hi Les,

    Yes all my other sites use RWW and some RPC/HTTP, but they all have a
    fixed IP. I use as well so I could deal with it that way.

    However, this partiicular site is getting an upgraded ADSL with a
    fixed IP Saturday week. I was hoping that there was a simple
    workaround in the interim.

    Most small organisations migrate from POP to SMTP, so I thought all
    these related routing issues had been dealt with already.

    All the other sites I deal with have only internal office workers,
    this is the first time folks are in the field and rarely visit the
    main office, hence the issue. The computers used by the field workers
    are workgroup boxes and just use the net and the ISP's POP/SMTP


    Kev, May 4, 2006
  7. A temporary workaround would be to forward a copy of all email from Tony's
    Exchange mailbox to an ISP hosted pop box, and Tony could pick it up there.

    Create a contact in ADUC like TonyPOP, and give it the email address of
    (the ISP hosted pop box). In Tony's user properties (one of the
    exchange tabs), delivery options - enter the external email address and
    elect to have mail delivered to both locations.

    Be certain that your Exchange POP3 connector is *not* picking up mail from
    though, otherwise you'll get a serious loop happening ;-)
    Les Connor [SBS Community Member - SBS MVP], May 4, 2006
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