We have users who have more than one exchange account on their Outlook profiles, some are fine and do not get prompted for passwords and some do. Of course it has to affect the CEO!
We had the issue before with 2010 and it still is a problem with 2013.
We have tried various bodges and workarounds up until recently I was using this - http://www.codetwo.com/freeware/autologon/ to keep the boss happy but this seems to fail now and always ask for a password no matter what.
The setup is like this:
Outlook 2013 connected to Exchange 2010.
User logs on as google\joe.bloggs
mailbox #1 is email@example.com
mailbox #2 is firstname.lastname@example.org
mailbox #3 is email@example.com
They are separate companies but on the same Exchange, we have added unique identifiers as we cannot obviously have the same username more than once.
Mailbox #1 is google\joe.bloggs
Mailbox #2 is google\joe.bloggs.1
Mailbox #3 is google\joe.bloggs.2
So different email addresses but all 3 user accounts are located in the same Active Directory.
At this point I am so desperate for a fix as this crops up everyday and I am running out of ideas and excuses as to why this hasn't been fixed.
Any help would be appreciated or if something is not clear or doesn't make sense please let me know so I can do my best to reword it.