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

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    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 Outlook® 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.

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