Hello Eric! We recently received word that a recent update to Outlook was causing sync issues which may be related to what you're seeing here. Microsoft advocated for a downgrade as well, so it sounds like this might be what was happening. Details on that Microsoft post can be found here:
If you see this again please submit a ticket with us as we'd be happy to dig into it for you. Have a good one!
Kyle Kerst
IT Coordinator
SmarterTools Inc.
www.smartertools.com