Years ago we had Exchange 2003 servers with one running OWA. Lets call the OWA server SRV-OWA-2003. This use to have an alias of webmail.mycomp.com.
Several years after our Exchange 2007 enviroment was brought up and user started to migrate to the 2007. The new OWA server had an alias of mail.mycomp.com.
We decided to put in an Exchange 2010 enviroment so we thought we would take all the old mailboxes for the disable users and move them to the Ex2003 box, then back it up, archive it and decommission it. Then we would use install the 2010 servers, move the active mailboxes from 2007 over to 2010 and then decommision 2007 as well.
Well the problem we have is that 2010 was brought up and 2007 and 2003 still exist. That is not so bad except for one thing. The 2010 consultant reused webmail.mycomp.com as the OWA and autodiscovery name for the front end client array. Lets call it CASHUB.
Even though we have DNS records entered for webmail.mycomp.com internally and externally, our Outlook clients have an issue when Outlook Anywhere is enabled. When we check the settings it shows it is pointing to webmail.mycomp.com, however when we check the connection settings (right clicking on the outlook icon in systray) we see the proxy is correct, but the Server Name is referencing the old 2003 OWA server called SRV-OWA-2003. This causes the Outlook 2010 clients to constantly prompt for a username and password.
How is the Outlook client seeing the old 2003 server instead of the new 2010 server as webmail.mycomp.com?