Hello All,
I am having problem connecting to our Exchange 2013 from Outlook 2016 application running on external PC (outside LAN) or internal PC but not joined to Domain using auto-discovery. However there is no issue connecting to Exchange from Domain joined PC, auto-discovery working fine and connects to Exchange.
The problem is, when I try to setup Exchange profile by entering name, email address and password, it tries to find Exchange server through auto-discovery and after few seconds it prompts for entering password where my email-address is shown as user-name. Even after I put my password correctly, it still opens-up the same password prompt window. It keeps on coming again and again, no matter how many times I put my correct password.
Sometime, though, it throws another message "An encrypted connection to your mail server is not available. Click next to attempt using an unencrypted connection.". Then selecting unencrypted connection, eventually it fails and give me option to choose Activesync or IMAP/POP3.
From Domain-joined PC and when logged-into Domain, Auto-discovery seems working fine because Outlook 2016 can find the Exchange and able to create profile and connect to server without any issue. It does not prompt for any password since I am already logged-into domain. Also from Smart-phones, Outlook or other Email clients can be setup to connect to Exchange and no issue with that. Only with computers which are not on domain. Not sure what is causing this.
I tried using Activesync, but got to know its for lite-version of email clients and not for full-featured client which Outlook is.
My guess, the issue is lying somewhere in Exchange configuration the way authentication is being handled for outside domain. I don't think its an issue with Outlook application, I have tried it on different PCs with 2016 and 2013 version of Outlook, same result.
I have had lots of time spent to troubleshoot this issue, no luck ye. I will appreciate any advice which may help to resolve the issue.