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Over the last couple of weeks we have been experiencing some odd issues mostly related to Calendars, such as:

  • Calendars don't stay in Sync across devices or delegates.
    • Delegate A changes appointment Location, but it doesn't show up on the original users calendar or any other Delegates.
  • Appointments just randomly go missing from users Calendars (this is not specific to one mailbox).
  • Mail folders disappear - don't show up as deleted and are missing from Recovery.

I've tested mailboxes using the New-MailBoxRepairRequest CMDLet and they all test out fine. There are no errors in the Event log regarding these issues.

Any recommendations for next steps? I was contemplating just creating a new database and migrating the mailboxes there but I fear it won't resolve any issues.

The Environment is:

  • Exchange 2010
  • Outlook 2011 for Mac. 12 iMacs.
    • Everyone has an iPhone or Android and some users have iPads.
  • Calendars are shared universally along with Contacts.
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I think you have a combination of two problems.

The first is icloud. Check the affected users to see if they have icloud backup turned on for calendar and contacts. If they do then turn it off. You don't have to disable icloud entirely, just the calendar and contact backup.

Second is cached mode in outlook. I've seen some crazy calendar sync problems with delegates and cached mode. If possible you should disable cached mode on both the delegate and the delegator. Be careful because if you are having this problem the someone will end up with missing appointments when you turn off cached mode. I suggest you print or pdf the calendar from list view to recreate missing appointments.

  • iCloud was not an issue as that is disabled on all of their devices. Caching also wasn't the problem as I've even setup brand new profiles. It appears as though there may have been an issue with a Client Access service - a memory leak of sorts. Time will tell. – Chris Sep 23 '13 at 20:30

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