Hello,
So we migrated 153 users from Exchange 2007 to Exchange 2013. Coexistance is still in place for a few test mailboxes, however, I have 12 users out of the 153 who are constantly getting password prompts. The user infrastructure is all MAC based clients using Outlook 2011.
Troubleshooting:
- Autodiscover: Originally, I thought it was misconfiguration but all of the values are identical to the Exchange 2007 server and have verified all virtual directory authentication values are the same. I would think if there was an issue with virtual directory configuration it would be more widespread.
- Outlook 2011 client: I have tried both manual and auto configuration within the client and get the same result. I've tried changing the username format to just john.smith@domain.com, domain\john.smith@domain.com, and just AD username, but still get authentication failures. I have tried to set up one of the problem accounts on a different MAC that the user has never logged onto and get same result. I have deleted the keychains entirely from the MAC device and reset the passwords to match the AD account and get same result.
- OWA: These users have no issue logging into OWA to send and receive mail.
- Windows Based Outlook 2010 client: I have logged into a Windows server with some of the problem accounts and Autodiscover and authentication works successfully without a glitch. The account is created successfully and have left the client idle for long durations with no authentication pop-ups.
At this point I am thinking it's related to the MAC based client, however, my experience with MAC clients is limited so I am hoping someone with more knowledge can provide some advice on other steps to try or where to look. Other thoughts are that security settings for these AD accounts may be causing authentication issues somehow and may be something I've overlooked. Also, could this be more related to the keychains? As I mentioned, I completely deleted the keychains and reset the password to match the AD account to which I was currently logged onto, which was the Administrator account rather than the user I was trying to troubleshoot.
Please help by sharing your experience, ideas, and any other troubleshooting steps I can perform.
Thanks!
Kristopher L.