You might run into an issue with Office 2016 where you’re trying to get an email older than what your cache is setup to capture and Outlook just won’t let you. Cache mode used to let Outlook connect directly and view files directly on Exchange, but this functionality is no longer available.
There are two workarounds to this issue
- Connect directly to the online version of your email via https://portal.office.com or https://outlook.office365.com
- Extend your cache mode to accommodate the time frame of the email you are looking for
In my case I had a 12 month cache, which I extended to 24 months
After I restarted Outlook, I noticed I could browse to those emails again.