I will try and be as detailed as I can here. We recently upgraded from Exchange 2007 to Exchange 2013. Most of the users have Outlook 2010 and 2013 (even mix).
Here is the problem. People from outside the office can login without being asked for logins and passwords multiple times (twice) every time they open their Outlook. Phones work perfectly and I can login with Outlook from home to their server without being asked for passwords. Its the people in the office that keep getting asked for passwords and they are also getting certificate problems in the office. Its not all users in the office having password prompt errors. We are in the middle of going to everyone and creating new mail profiles in the hopes that might solve the problem.
If the profiles don't make a difference, do you guys have any suggestions?