If I remove and re-add their permissions, but then not automapping and adding the mailbox in as an additional mailbox the problem goes away. Users having the problem all have access to shared mailboxes that are automapped. I've narrowed it down to what I think is a shared mailbox issue. I've done a lot of research and noticed a lot of other people have the same issue but I've not been able to find a definitive answer. I think this is because once the autodiscover.xml file is regenerated on their computers, the next time they do into Outlook it'll cause the logon prompts. However the next day or two the problem usually returns. OSTs and autodiscover.xml (and occasionally deleting cached credentials in Credential Manager) helped fix the issue. We found that deleting their mail profile, their. However, after user's had Office upgraded to 2016 lots of users started getting logon prompts when opening Outlook. During the transition Outlook 2010 clients had no issues, whether the mailboxes were on Exchange 2010 or 2016. During this time we were also upgrading out clients from Office 2010->2016. Over the last 6 months we've migrated from on-prem Exchange 2010->2016.
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