I was just made aware of this useful tool by Microsoft Support – the Microsoft Support and Recovery Assistant for Office 365 (also known as ‘SaRA’).
Even better, it’s not just for Office 365, other Office products can be scanned using this tool such as Outlook in Office 2010, 2013 and 2016.
The article above has a step by step guide for scanning Outlook for problems. It takes a few minutes to run, but will identify a bunch of possible issues you may have. But, from the results I see, I’d say everyone should run this tool regardless!
For example, my scan came up with this as one of the issues found:
The link goes here which then goes into details about the problem. I had noticed in Outlook 2016 by default, that users had sometimes mentioned they could no longer delete items from mailboxes they only had Inbox access to, and I assumed this was a change in behavior from Outlook 2010. This tells you how to toggle that setting if you’d rather the deleted items go to the other person’s mailbox, which removes the need for the delegate to have access to someone else’s deleted items.
If I’d run this at the start of the Office 2016 deployment during testing, it would have given me a better idea of potential issues that might come up. Here’s another one:
That’s not ideal at all! Again the link goes into more detail and this one seems really important –