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Office 365 Shared Mailbox Not Updating For One User Only

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I have one user who's shared mailbox won't update. We are using O365. I have attempted to put Outlook 2013 in cached mode and without and still no change. Sometimes I can remove the mailbox and re-add it and it starts working but not always. This is only effecting 1 user out of 5 and the other 4 aren't having any issues and all 5 machines are configured the same. 


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