This is actually an IIS issue with Server 2008 R2 (the operating system Exchange 2010 was installed on) that’s resolved by a hotfix. Turns out this issue was recently addressed via “Outlook Anywhere users prompted for credentials when they try to connect to Exchange Server 2013”. After a search through my OneNote I realized I previously had a discussion with some people I know from Microsoft Support regarding this issue. When I was approached with this issue/symptom it sounded familiar. Sometimes the prompts would be when connecting to Public Folders while other times mail or directory connections from Outlook to Exchange. While this was somewhat working, they also immediately noticed users were randomly being prompted for credentials, resulting in a negative user experience. At this point all of their Outlook Anywhere clients should have been connecting to Exchange 2013 & then been proxied to Exchange 2010. As part of their migration process they pointed their Exchange 2010 Outlook Anywhere namespace (let’s call it ) to Exchange 2013 in DNS. I was working with a customer who had Exchange 2010 & were in the process of migrating to Exchange 2013.
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