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If the data files are pst files, the problem only occurs if an email account is delivering mail to a pst or the pst is enabled for reminders.
There a few workarounds you can use to see your tasks again: If you need to group by the Start date or Due date, open View Settings, Group By.
There are known issues that cause some email clients, especially older clients and those on some mobile devices, to provide inconsistent and unreliable updating of calendar information via Exchange Active Sync.
An exact cause is not always known and can vary from client to client.
The reason for this problem is when the user runs the Outlook 2016 in any of the cached modes with Exchange or Office 365 they start facing this type of issue.
Many features of Office 365 enables us accessing Outlook on the web, access to cloud-hosted versions of server provides service of Office application which is more secure.
Untick Automatically group by arrangement and select Due Date in Group items by selector.
To change the view on the Task list in the To-do Bar, right click on the row above the tasks that reads “Arrange by” and choose a different arrangement, untick Show in Groups or choose View settings to customize the view.
generate in your account then it means that the admin doesn’t give the permission to that particular users for accessing that calendar folder.Sometimes even after clearing the cache user gets the same problem of Office 365 calendar permissions not working in Outlook.