Hello,
I have a weird issue with connecting outlook to our Exchange 2013 Server, I have a authentications loop if I use the email address of @abcdtownship.on.ca, but if I use the second email address of abcd.ca it work fine from the outside of the network. From the inside of the network I have a authentication loop if I use the email address of @abcdtownship.on.ca, and also with abcd.ca, the only way I got it connected is if I use the email address of @abcd.office, the issue with this I have no MX record pointing for abcd.office.
I did the test from https://www.testexchangeconnectivity.com/ everything pass from there with the email address of @abcdtownship.on.ca
What could be the problem?
Here my setup.
Inside domain is abcd.office with a 2008 R2 AD.
Our default email address is @abcdtownship.on.ca. We are planning to move all our email to this address in future @abcd.ca.
My SSL SAN are these and they are from entrust
autodiscover.abcdtownship.on.ca
mail.abcdtownship.on.ca
autodiscover.abcd.ca
mail.abcd.ca
DNS are these
A record autodiscover.abcdtownship.on.ca pointing to 1.1.1.1
A record mail.abcdtownship.on.ca pointing to 1.1.1.1
A record autodiscover.abcd.ca pointing to 1.1.1.1
A record mail.abcd.ca pointing to 1.1.1.1
MX record abcdtownship.on.ca pointing to mail.abcdtownship.on.ca
MX record abcd.ca pointing to mail.abcd.ca