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Trouble sending local exchange users emails via exchange server when they are offsite

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  • Trouble sending local exchange users emails via exchange server when they are offsite

    Hello,
    I configured the SBS Exchange 2003 component for an office. Everything works excellent except for one part that I cannot figure out. The users have 2 accounts in the outlook client (one pop3 and one Exchange Mailbox). Normally the users use POP3 for incoming and outgoing mail. However, to accomodate one piece of software, I did set up Exchange server to allow sending mail via SMTP through a product called XWALL. I disabled SMTP incoming mail via the server.
    In order to have a valid return address applied for these outgoing emails via the Exchange Server, I entered the users email address as a primary SMTP address in the user's Email Addresses Tab ( via the GUI for Server Management> Manage Users> particular user > Email Address Tab). So now, outgoing emails will have a valid return address. This works. One scenerio, however, presents a problem.

    When the user leaves the office with their laptop and some else at the office sends them an email via their Outlook using the "Exchange Server" Account, the message gets routed to the Exchange Store, and never leaves the site. I believe according to the snippet below from Microsoft's Technet, that the "message categorizer" finds the address and determines that this message should be delivered to the local exchange store for the user. This is the end result at any rate. I highlighted what I think the issue is in the section below.

    <---------------------------------------------------------------------------------------------->
    From Microsoft's Technet Library (I'm not allowed to paste in URLs yet)
    1. The message is submitted to the advanced queuing engine in one of two ways:
    2. If the message was sent using a Microsoft Office OutlookŪ Web Access or Outlook (MAPI) client, the Exchange store submits the message to the advanced queuing engine through the store driver.
    • If the message was sent using a Post Office Protocol (POP) or an Internet Mail Access Protocol (IMAP) client, SMTP passes the message to the advanced queuing engine.
    1. The message categorizer then queries the global catalog server with the recipient address to find the user. If the recipient address is not in a recipient policy, or if a matching recipient with a proxy address does not exist (the recipient address will not be stored in Active Directory), the message categorizer determines that the message is bound for a remote domain.
    <--------------------------------------------------------------------------------------------->

    My question is, how can I keep this from happening. As it is, the recipient will not receive the message until they return to the office, log into the domain and then, via send and receive, they "receive" the message via the exchange store. I sincerely appreciate any insite into this as they have several users going offsite a good part of any day and are still relying on getting emails from the office via their webmail site when out of the office. Sorry if the message appears longwinded, but I wanted to describe the issue as accurately as I could. Thanks for your understanding.

  • #2
    Re: Trouble sending local exchange users emails via exchange server when they are off

    Your problem is that you can't really deploy Exchange in a piecemeal fashion like this. Exchange is designed to be responsible for all email for the domain.

    The problem is occurring before the email reaches Exchange. Outlook recognises that the email matches an email address on an internal mailbox. It will then treat that email as an internal email, queue the email until Outlook can connect to Exchange.

    Your best option would be to use Exchange for all email, dumping POP3 completely. Use Outlook over the Internet to allow connections over the Internet to the email server. Instructions for Outlook over the Internet are in RWW.

    Simon.
    --
    Simon Butler
    Exchange MVP

    Blog: http://blog.sembee.co.uk/
    More Exchange Content: http://exchange.sembee.info/
    Exchange Resources List: http://exbpa.com/
    In the UK? Hire me: http://www.sembee.co.uk/

    Sembee is a registered trademark, used here with permission.

    Comment


    • #3
      Re: Trouble sending local exchange users emails via exchange server when they are off

      First of all, Thanks to the site for all the help via FAQ's and articles that I've used over the past couple years to set up and solve network and server issues. As I came to do Server support from a the Desktop support arena, this site has been an indespensible tool. You've made the steep learning curve easier to negotiate.

      Followup:

      Please don't hesitate to correct me if i misunderstand the boundaries of Outlook/Exchange. I do believe that the mail is getting delivered to the recipient's Mail Store Folder after the sender hits "send and receive" as opposed to being queued. While the intended recipient is still offsite, I used Outlook's WebAccess to log into the intended recipient's exchange mail folder on the server, the messages are in the intended recipient's INBOX. The part where outlook or exchange recognizes it as internal address and keeps it there is what I would like to defeat. Basically, I would like to Hide this information from the lookup for those users who take laptops offsite.

      As this is the only issue I have with the Exchange setup, I am hopeful it can be resolved without altering the overall server/exchange setup or adjusting all the user's Outlook settings. Thanks again to the group for their insite.
      Last edited by nobilis; 1st June 2011, 19:31. Reason: misinterpreted use of "queue" i believe

      Comment


      • #4
        Re: Trouble sending local exchange users emails via exchange server when they are off

        You can't stop Exchange from recognising it is an internal mailbox.
        As I have already said, Exchange isn't designed to be used in this way.

        With Exchange, email is stored on the server, not Outlook. Outlook is just an interface to the mailbox, like OWA, ActiveSync etc.

        Simon.
        --
        Simon Butler
        Exchange MVP

        Blog: http://blog.sembee.co.uk/
        More Exchange Content: http://exchange.sembee.info/
        Exchange Resources List: http://exbpa.com/
        In the UK? Hire me: http://www.sembee.co.uk/

        Sembee is a registered trademark, used here with permission.

        Comment


        • #5
          Re: Trouble sending local exchange users emails via exchange server when they are off

          Thanks Simon. Next go around ( with SBS 2011) I'll prep myself to have Outlook and Exchange, OWA et al set up in finer fashion. I appreciate your insites. Keep well.

          Sincerely,
          Patrick

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