The problem being addressed here is that the iCloud add-in gets disabled each time outlook is closed and restarted. This is only a problem for people who want to have their iCloud synchronized with their Outlook. This solution should be applicable to Win 7 and 8.1 and Outlook 2010 and 2013.
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Start Menu > regedit
- Select : Computer/HKEY_CURRENT_USER/SOFTWARE/MICROSOFT/OFFICE/OUTLOOK/ADDINS - Apple.DAV.Addin -
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On the right, double-click on LoadBehavior and check the value: if it say 0, set it to 3.