If you want to do both thats a two way sync, you have to have the same contacts in your bold and in outlook to do that or it will mess up. I'm guessing you want your bold contacts in outlook or vice versa. To do that, go to sync options, select either outlook to bold (if your contacts are in outlook and want them in the bold) or bold to outlook (if you want your bold contacts in outlook), then after that finishes, select both.
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