Have you checked the Apple iPod support forums?
http://discussions.apple.com/categor...categoryID=146

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Milly Staples [MVP - Outlook]

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After furious head scratching, zoman asked:

| Using Office 2003. ipod will not sync to calander or contacts. Screen
| does not appear asking to let ipod access outlook. ipod shows it's
| updating but never updates.Apple says it's Microsoft 3rd Party they
| dont support. Yet they advertise it works with Outlook.