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Outlook clients using Outlook Anywhere cannot connect.

Posted on 2008-10-23
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Last Modified: 2012-06-27
I've been unable to get Outlook Anywhere to work for any remote clients using Outlook 2007.  I have an Exchange 2007 server on my relatively small domain and it is connected with 1 nic to my network with an internal IP and the 2nd nic is connected with a static address to our ISP (probably unsafe but was having trouble getting this to work otherwise).

Everything internal works fine (however we get a certificate error whenever outlook is launched because our certificate is for *.domain.com and the server is exchange.localdomain.local).  This is an issue I will address at another time since it at least works.  Remotely our OWA works great and is running over SSL with the proper cert.  

I went through exchange_genie's howto at:
http://exchange-genie.blogspot.com/2008/02/configuring-outlook-anywhere-for.html

and verified all the changes.  RPC over HTTP is setup, it is listed in IIS 7, RPCProxy.dll is allowed, I used EMC to enable Outlook Anywhere, with Basic Authentication and verified all the Valid Ports in the registry.  

Outlook itself from outside the company is setup using exchangeserver.localdomain.local and the connection tab has outlook anywhere's option checked off using SSL only and Basic Authentication.  

My mind is a bit mushed up now so if anyone can think of some alternative ideas to check - that would be great!
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Question by:jaelae
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by:Scripting_Guy
ID: 22791599
If your Outlook outside the company is setup to use exchangeserver.localdomain.local, then this is where you might start looking. This DNS-Name is (if at all) only valid if you're using your DC as DNS-Server. Use the same DNS-Name / IP Adress you use for accessing OWA from outside your company.

Also note that if you're using a self signed Certificate, you will need to manually deploy it to every Client using Outlook Anywhere.
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by:jaelae
ID: 22795767
The certificate is a wildcard one issued by godaddy and appears to work great over OWA.  It seems to be a configuration issue in Exchange - rather than on the client.  I'm using GFI MailEssentials for antispam - and Microsoft Forefront Exchange Security for antivirus.  Aside from this it is just using the internal firewall which I have even disabled to verify nothing is being blocked.
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jaelae earned 0 total points
ID: 23283528
I have since reloaded a new Exchange Server from scratch and this is no longer an issue.
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