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Import Mail, Contacts, and Other Setting... > Merge the Contents into Your New Mai...
Merge the Contents into Your New Mailbox
The easiest and most common approach is to merge the contents of your PST file into your new mailbox. The result is that all your old mail is imported into Office 365, using the same folder structure and with the same content as before. Choose this option when you want to import your contacts, calendar settings, tasks, mail, and other details from your previous email account into your new Outlook account. The content will automatically be copied into your Office 365 online mailbox.
To import a PST using Outlook 2010:
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Start Outlook.
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Select File | Options | Advanced | Export.
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Select Import From Another Program Or File, and then click Next.
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Select Outlook Data File (.PST), and then click Next.
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Browse to the PST file, choose how you want to manage duplicates, and then click Next.