I ran into an issue today that I could find very little information on so I figured I would put this out on the blogsphere in case it might help someone else.
I recently upgrade my Exchange server to Exchange 2007. I access it through ISA Server 2006 using Outlook Anywhere most of the time from a machine that is not joined to the domain.
I thought everything was up and working fine until I went to create a outlook contact for the first time since the upgrade. It would not let me save the contact and gave me a message indicating “Outlook must be online to complete this operation”. I was online. In fact I was online and receiving email.
I found out you can start outlook with the /rpcdiag flag to give some information as to what is going on with connectivity.
This dialog would show 3–4 Directory operations spun up and either connecting or disconnected.
At first I thought it was an issue with how I had published it in ISA Server but eventually gave up on that as I was essentially server publishing port 443 direct to the Exchange server.
I found one article that alluded to a similar problem that talked about setting up a remembered password in Vista for all machines with a particular domain name. Didn’t sound like a great idea but got me to thinking that it could possibly be an authentication problem with the Active Directory box. The directory request was traveling from Outlook, to the Exchange Servers RPC over HTTP connector and then having to leave the box to hit the AD box. Could it be an issue with double hop impersonation? Still not sure but as a test I installed the Active Directory role on my Exchange 2007 box and voila the problem went away.