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Exchange 2007 Outlook Anywhere

We just setup a new Windows Small Business Server 2008 with Exchange 2007 (with sp3 and all the rollups) and configured Outlook anywhere.  Outlook anywhere doesn't seem to work from outside the network and only works inside the network when both the server in the Outlook config setup and the URL for the proxy server are set to SERVERNAME.DOMAIN.local (both http and https work inside the network).  If I set it to SERVERNAME.DOMAIN.com (which would be the same externally) it connects but it asks for a username/password and no matter how it is entered it doesn't validate (DOMAIN\username, DOMAIN.local\username, etc).  Any ideas on what to try next?

Also I should mention that Outlook web access works fine too.
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bdhtechnology
Asked:
bdhtechnology
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1 Solution
 
MegaNuk3Commented:
Do you get any certificate errors or warnings when opening OWA?

Have you tested Outlook anywhere from www.testexchangeconnectivity.com ?
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bdhtechnologyAuthor Commented:
It is a self signed certificate but I have installed it on the computer for testing and OWA does not give a certificate error in Internet Explorer.  

The Outlook anywhere test from www.testexchangeconnectivity.com fails because it is a self signed certificate.  

I have gotten this to work previously using a self signed certificate so I know it can be done.
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MegaNuk3Commented:
If OWA works without a cert warning then RPC/HTTP should too.

When testing internally open outlook with /rpcdiag to confirm outlook is connecting over HTTP and not TCP.
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bdhtechnologyAuthor Commented:
It never gets to a point where it connects.  It just asks for the username/password over and over.  The status just says connecting.

If I switch everything to .local it says TCP/IP so it doesn't appear that RPC is working with .local either.
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MegaNuk3Commented:
What are the names on your self signed cert?
Have you tried Basic auth in your HTTP proxy settings?
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bdhtechnologyAuthor Commented:
I am just going to buy an SSL certificate to eliminate that.  Should the SSL certificate be SERVER.DOMAIN.com or mail.DOMAIN.com?  They typically access everything by using mail.DOMAIN.com now, plus then it could be used for a future server.  What do you think?
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MegaNuk3Commented:
Use mail.domain.com
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bdhtechnologyAuthor Commented:
Once the SSL certificate was purchased and installed the Outlook anywhere from www.testexchangeconnectivity.com went through.  The main problem was that I needed to forward ports 6001,6002 & 6004 through the firewall.
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