I'm migrating from Exchange 2010 to Exchange 2013 and on the final stages. I pointed the external and internal DNS records to Exchange 2013. I moved one mailbox to Exchange 2013 and then tried to create a new Outlook client profile and bring the mailbox up however the client would not connect. It stated trying to connect encrypted and unencrypted. It did not work. I checked nslookup and the IPs are all set pointing to Exchange 2013. I then checked my certificates. I have a certificate that is a wild card. When I checked assigned services on my wild card it had IIS and SMTP assigned. Also in IIS on the default site bindings what should you use as a certificate on the two https settings? Originally they were the local generated certificate. I changed them to the wild card no luck. Please assist.

Try running through this and see if it gives you some ideas on what is wrong:

https://testconnectivity.microsoft.com/

Hi Sgtjd,

Any update?

Best regards,

I received professional help from Microsoft in regards to the connection. The first thing is permissions were not set right on the receive connector on the old exchange server. the second step was the internal DNS was still pointing to the old server even though everything was correct. A new forward lookup zone was created just for the A record address to the new server. Only the FQDN and ip address were filled out. the Host name block was left blank.