Hi.
I've been spending most of this week testing and troubleshooting on our Exchange server where we host several companies email. We're currently migrating from Exchange 2010 to Exchange 2013 so I've added a 2013CAS server and a 2013MBX server. I have configured them and they work fine except for Outlook Anywhere.
Out current Exchange 2010 server has the below OutlookAnywhere configuration. A wildcard certificate is installed and the CertprincipalName has been set according to this on EXCH,EXPR and WEB. (This solved an earlier problem where XPs couldn't connect to our then single Exchange 2010 server)
I'm now testing the mailbox migration from 2010 to 2013 which needs to be done as smoothly as possible so we don't have a few hundred angry users calling us when mailboxes have been moved.
We need to support XP with Outlook 2007 and 2010 on. Also need to support Win7 with 2007/2010/2013 installed. Oh last but not least we also have customes logging in to Citrix servers with Outlook 2010 installed. The Citrix servers (2008R2) are members of the same domain as the Exchange servers.
The best configuration (smoothest) I've ended up with on the 2013 CAS server is the below.
This configuration migrates mailboxes located on all the mentioned clients with no manual configurations required. But afterwards I need to enter passwords each time Outlook is started on the XP+2007, XP+2010 and WIN7+2007 machines. If I change the proxy authentication on the clients to Basic they log on without the password prompt, but eventually Autodiscover fetches the above configuration and the proxy authentication is changed back to Ntlm leaving me with password prompts at start again.
As I wrote I've spend most of this week testing this, and this is the best config I could find. I tried many different authentication settings but so far I haven't been able to find the perfect settings that removes all password prompts.
I'm almost ready to go ahead with the above configuration telling customers that because they are using old software they have to enter a password each time they start Outlook, but to be honest I'm not very proud of that solution :(
So if anyone can point out something else that I should try then pleeeeease do so :)
Best
Thomas