I'm attempting to setup POP accounts on Outlook 2013 for roaming profile users in an RDSH pool. I have policies setup for folder redirection on the Documents folder and a policy for default PST location (among others). I'm currently experiencing an issue with the password prompt reappearing when a user opens Outlook on another server in the RDSH pool. All other settings are carried over including the pst.
I have setup a login and logoff script to copy the Local AppData in the Roaming AppData so it's picked up with the Roaming Profile. However, the issue still persists. I also tried using WhatChanged to track where the password is being stored (user registry or profile folder) but found nothing.
A little insight into where the 'Save password in your password list' checkbox stores the goods.