Using Classic Outlook on Windows for personal email, calendar, and contact management
I'm going to take an educated guess and say that this is just another issue that Microsoft is going to ignore and let continue. Outlook is not usable with this bug. Clearly the developers at MS are more interested in moving buttons around and changing the GUI than actually fixing errors and issues that affect usability. The whole time that they are failing to resolve these types of issues with 2016 and O365, they are busy blocking your old versions that actually work correctly, such as 2010. Doing this on a "ohhh it's for your security" basis, which is complete horse ****. It's done to make MS more money.
I've never seen such a dysfunctional company.
Oh, and if you want to know how to go back to running Outlook 2010 on Exchange servers by defeating Microsoft's elementary level block, let me know. I'll be doing a YouTube video on that later today.