Getting an Off-Site Outlook Install to Connect to SBS 2003

When you look at the many wonderful sites devoted to Microsoft’s Small Business Server 2003 (SBS 2003), one of the many items touted is the ability to access Outlook date over the internet, using RPC over HTTP.  From the various descriptions, it would seem to be an easy thing to do.  However, what do you do if the computer is not on site (for example, it is the home machine of the CEO for the comany in question).  If you follow the instructions found all over the web (like here or here or here), it appears that it should just work.

Silly man/woman!  This is Microsoft, not Apple!

Fortunately, the answer is both simple and complex.  The simple fact is that Outlook needs to verify that the account is set up correctly the first time it tries to connect.  Since it cannot “check names”, it fails.

So, the simple answer is to create a VPN connection, then open Outlook (to allow it to verify the names of the user and the server), and then let it create the local mailbox.  Once it does so (even before it finishes downloading all of the data), you can close Outlook, remove the VPN (if you wish) and the RPC over HTTP should work without fail.

Assuming, of course, that you had the Internet Connection Wizard (ICW) open up the proper ports.  Oh, and that you have the SBS box be the DNS server (as is MS’ wish).

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