A few obvious things to check (hope it's not insulting!)
1. In the bottom of Outlook window it has status. Should read 'All folders are up to date. Connected to: 'Name describing your Exch/O365 account'
If there is an issue with a specific folder, you can resync the folder in Outlook. To do this, follow these steps: Right-click the folder, and then click Properties. Click Clear Offline Items, and then click OK. On the Outlook 2010 ribbon, click the Send/Receive tab. Click Update Folder. Sync Issues Contains all of the synchronization logs. This folder is helpful if Outlook is having trouble synchronizing — for example, there is an item that you see in the Office 365 OWA (Outlook Web Access), but not in Outlook — or you are not getting new mail in some folders when using Cached Exchange Mode.
2. In the ribbon menu, under tools - check that the toggle slider for 'Online/Offline' is set to online (shows green)
Next to this is the buttons for Sync Status and Sync Errors. If you open up these windows are they blank, or have any diag messages. Keep them open and monitor as yo use Outlook and make changes.... Anything significant observed?
A few obvious things to check (hope it's not insulting!)
1. In the bottom of Outlook window it has status. Should read 'All folders are up to date. Connected to: 'Name describing your Exch/O365 account'
2. In the ribbon menu, under tools - check that the toggle slider for 'Online/Offline' is set to online (shows green)
Outlook 2016 Could Not Synchronize Record Error -19703 Windows 10
Next to this is the buttons for Sync Status and Sync Errors. If you open up these windows are they blank, or have any diag messages. Keep them open and monitor as yo use Outlook and make changes.... Anything significant observed?