Outlook Calendars Not Syncing

Contributor II

We use Office 365 and most of our Mac users are using Outlook for their email and calendar needs. We're seeing an issue where certain people, usually leaders who have lots of meetings are encountering sync issues where they fail to show up for a meeting because it never got to their Outlook. These tend to be situations where they have an administrative assistant who manages their calendar for them. The calendar will be synced properly on the assistant's Outlook, but not on the leader's. A "fix" for us has been to empty the calendar cache in the leader's Outlook. That forces a re-sync, but can be somewhat time consuming. Has anyone encountered this and has a fix? Is this just to-be-expected behavior from Outlook? Any solutions? Appreciate any help you can provide!