Outlook anywhere headaches

I have been messing around trying to get Outlook Anywhere to connect to our new Exchange 2007 installation.  I have been battling through various hurdles like getting getting a correct certificate generated, getting that certificate installed on a client pc and testing the connection.  I have been able to get a SSL connection to OWA so I figured once that was the case, Outlook Anywhere should work as well…. not.

If you Google “outlook anywhere problem” you will get a massive amount of hits, basically, it’s a pain in the ass.  I also discovered it is even more of a pain of the ass if you have Exchange 2007 running on Windows Server 08.  Evidently Outlook Anywhere does not like IP v6, you need to disable it.

I was further baffled when I was able to connect to the RPC proxy in the browser by going to https://myexternalurl.com/rpc  After supplying my credentials I got a blank screen on a secure connection just like I was supposed to.  I then went a step further and used RPCPING to verify that I was indeed talking to my Exchange server and it was accepting my credentials, it was. Well what the hell then?

Every time I would try to connect with my Outlook client I would be presented with a credentials dialog, I would provide them only to be slapped in the face with an “Unable to connect to your exchange server error…”

Well after looking at countless pages filled with countless suggestions I finally came across one that worked.  They simply said to add two entries to the local hosts file on the Exchange server that looked like this.

192.168.1.10   servernetbiosname  (local server name)

192.168.1.10 servernetbiosname.domain.local  (fully qualified server local name)

That simple change did the trick!  I was able to connect.  Wow what a headache.

Now keep in mind this suggestion will only help if you already have established that you can connect to your Exchange server rpc directory.  If that doesn’t work you have more homework to do.