Outlook 2016 sharepoint calendar not updating

I have created some Calendars in Outlook and then instructed users to go to the Calendar and click the Connect to Outlook button and then accept the calendar.

I do this because the Scheduling Assistant in Outlook doesn't show me as busy during meetings scheduled on the Share Point calendar (in Outlook) and the same applies with the Group Calendar in Share Point.

I have to actually go into the calendar I didn't change, delete the event, and copy the new event to the calendar.

What I am looking for is a way to link the events so that when one is updated, the other is updated as well.

Last Updated: March 22, 2019 ISSUE Outlook 2016 connected to Office 365 does not show all content of a calendar folder opened in cached mode.

The issue reproduces in every new Outlook profile created and the calendar cannot be synchronized in cached mode.

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