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ryan_a-icsFlag for United States of America

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Outlook Anywhere in SBS 2008

I am using a SBS 2008 based server and am trying to configure Outlook Anywhere to work outside the LAN.  Currently, I have port 80 and 443 forwarded to the server.  I checked to make sure the RPC over HTTP protocol was installed - and it is.  I can work with Exchange all day long on the LAN (over TCP/IP), but am still unable to connect from WAN side.  I have configured the Outlook 2003 client on this system to "Connect to my Exchange server using HTTP" and have configured our external IP address (static BTW) as the proxy server in the settings dialog.  Does the server have to have a CNAME on our internet domain forwarded to it?  Is there something I am missing here?
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Alan Hardisty
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Have you installed a 3rd Party Trusted SSL certificate?

Microsoft recommend that you do to make this work:

http://technet.microsoft.com/en-us/library/bb851554(EXCHG.80).aspx
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I can't even get it to work without SSL (which shouldn't require a cert at all)...
It is designed to work with SSL - if you try to make it work without, you could mess things up.

I would suggest you buy a 3rd party SAN / UCC (multi-name) certificate from somewhere like GoDaddy as they seem to be the cheapest (www.godaddy.com).

Certificates names you will need are:

mail.yourdomain.com
remote.yourdomain.com
autodiscover.yourdomain.com
internalservername
internalservername.internaldomain.local
And it is impossible to use a self-signed cert?
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Alan Hardisty
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OK - I'll see what I can do to convince my customer that they need a cert.  I figured this would be a pretty cut-and-dried setup, but apparently I was mistaken!  I assume I'll be needing to set up the above listed CNAMEs in my domain DNS?  - ex.  remote.whatever.com, autodiscover.whatever.com    Thanks in advance for your responses!
If you mean your external DNS then follow my comments the third from the bottom paragraph. Your internal records will be taken care of by the wizard.
OK, sounds like a plan.  I'll see what I can do to make this thing work.  Thanks for your input!