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Do you have more than one "contacts" group in your Outlook ? Perhaps, you have more than one...and it is trying to sync with an empty group....
Note: BEFORE you start hitting delete ANYTHING in Outlook...you might want to backup your contacts ~File>export to a file ( .pst).... contacts
It might be worth a try to export contacts and then import and then try to sync
.....but that can be done when you have exhausted all efforts....and you are trying anything and everything....
I am running out of suggestions :)
Susan
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