This article explains why you shouldn't move to "new" Outlook 365 on Middlebury-provided computers.
Issue:
A toggle button in Outlook suggests trying the "new" Outlook 365.
Do I really need to do this?
Solution:
No. You'll want to keep the "classic" Outlook version as it is still the recommended version for a business setting as not all functionality is supported in the new version.
Read more in Microsoft's forum.