Certificate issue in outlook while connecting to exchange after adding the external host name in outlook anywhere.
In Exchange 2013 Server, under Exchange Admin Center - Servers - Outlook Anywhere -
Specify the external host name (for example, contoso.com) that users will use to connect to your organization.
By default it was Blank, Since i wanted to test the outlook anywhere feature for a user, I mentioned my external dyndns.org name here.
*Specify the internal host name (for example, contoso.com) that users will use to connect to your organization.
By default , my internal FQDN Name was already here.
Authentication method was - NTLM
Allow SSL Offloading was checked.,
Once i saved this, all of a sudden, 25% of the users got the Certificate error while connecting to the exchange and were not able to connect. To get rid of this, I tried by importing the certificate from exchange to the local PC's, it worked fine for few users and they were connected to the exchange, but for other users, the error still remains and not able to connect. Then to bring it to normal, in exchange server, i removed the External Host name for the Outlook anywhere and restarted the server. The issue still remains, now its continuously prompting for the password in the outlook for few users. In the outlook, connect to Microsoft Exchange using Http gets automatically enabled and also all the exchange proxy settings gets enabled. I strong feel, due to this automatically enabling of the exchange proxy setting, i am getting prompted for the password.
I would like to know, how to sort this issue on the server side to bring it to normal. We can disable the outlook anywhere as no user is connecting from outside. What we want is only the internal Users should be able to connect to exchange through outlook.