Hello,
I have just commenced a Exchange 2007 SP3 to Exchange 2013 SP1 migration following the following guide: http://blogs.technet.com/b/meamcs/archive/2013/07/25/part-1-step-by-step-exchange-2007-to-2013-migration.aspx
As per the above guide, my 2007 environment is now known as legacy.company.com and my 2013, webmail.company.com.
I'm using the same certificate on both boxes and it has the names autodiscover.company.com, webmail.company.com and legacy.company.com. All that seems to be working fine.
OWA is functioning perfectly, hitting https://webmail.company.com will pass the user off to https://legacy.company.com if the mailbox is on 2007. Alongside this, Outlook also has no issues connecting to 2007 mailboxes with the client proxy settings being reconfigured to https://legacy.company.com automatically.
My problem comes when a mailbox is migrated to 2013. OWA functions fine and presents the mailbox but Outlook is unable to connect, presenting the error:
There is a problem with the proxy server's security certificate.
The name on the security certificate is invalid or does not match the name of the target site webmail.company.com.
Outlook is unable to connect to the proxy server. (Error Code 0)
If I modify the Outlook client's settings and disable "Only connect to proxy servers that have this principal name in their certificate: msstd:webmail.company.com", Outlook connects and functions fine.
I'm at a loss and have tried everything I can think and find on google. Any suggestions would be greatly appreciated.