So here's what's happening. Our Active Directory domain is companyname.net, and our users' email addresses are user@companyname.net, due to some unfortunate crap that happened long before I got here.
Outlook 2010-2016 allows you to add multiple Exchange accounts (from the same Exchange server / domain) to a single Outlook Profile. MS has a KB article that says this is unsupported and can cause ...
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