I have previously asked about this question before here
and we have since resolved the autodiscover issues (testexchangeconnectivity.
com shows passes for both Outlook tests) but the problem persist.
Users can be happily using Outlook for some time and then suddenly, they are prompted to enter their username and password before they can send/receive emails again.
To compound matters the authentication window is easily lost behind other Windows and the average user doesn't realised they are being prompted but they notice their email not working, resulting in a support call.
If autodiscover isn't the issue anymore, does anyone have any suggestions on where we should be looking for the cause?
Thanks in advance.