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Are both the boss and user running in cached mode? Try turning off cached mode and see if they both update. If so, you may need to rebuild the outlook profile.
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Are both the boss and user running in cached mode? Try turning off cached mode and see if they both update. If so, you may need to rebuild the outlook profile.

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They are both in CEM. Turning it off causes all events created by the user to disappear off of their calendar. Turning it back on brings the events back, and also creates another calendar for the boss in the user's view. I shall test turning off CEM for the boss and see if it updates.
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They are both in CEM. Turning it off causes all events created by the user to disappear off of their calendar. Turning it back on brings the events back, and also creates another calendar for the boss in the user's view. I shall test turning off CEM for the boss and see if it updates.

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Turning off CEM for the boss did not work. As a side note, when the admin has CEM on, there are two copies of the boss' inbox and calendar. When it is off, there is only one.
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Turning off CEM for the boss did not work. As a side note, when the admin has CEM on, there are two copies of the boss' inbox and calendar. When it is off, there is only one.

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I have multiple users who have full access to their boss' calendar. They will add an event to the boss' calendar and see the event populate on their copy of the calendar, but it won't sync to their boss' copy.
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I have multiple users who have full access to their boss' calendar. They will add an event to the boss' calendar and see the event populate on their copy of the calendar, but it won't sync to their boss' copy.

Outlook calendar not syncing between editor and end user

Microsoft Outlook is a personal information manager from Microsoft, available as a part of the Microsoft Office suite. Although often used mainly as an email application, it also includes a calendar, task manager, contact manager, note-taker, journal, and web browser.