Click "Go" on the menu bar of your Macintosh's desktop, click "Applications" and double-click the "iTunes" icon. Or, click "Start" on your PC's desktop, click "All Programs" and "iTunes."
Click "iPod" or the name of your iPod and click the "Contacts" tab.
Click the "Sync calendars from Microsoft Outlook" box, and select "All calendars" in the sub-menu. Alternatively, click "Selected calendars" and select the calendars you want to transfer to the iPod.
Whereas iTunes does not require authorized access to synchronize calendar data from the iCal application to your iPod, Outlook restricts unauthorized access from outside programs. If you wish to transfer your Outlook calendars to the iPod, the iTunes program must be properly configured with your computer's Outlook program. According to Apple, Outlook's security feature sets an access time limit to protect your information and will ask you to choose the amount of time allotted for iTunes. Once the programs are configured, calendar events can be transferred to your iPod's calendar application.
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