So, this may or may not be a well known fact. I've known about it for awhile myself, but am just now sharing this with the public at large. After experiencing this problem myself, I found the same issue described in the Apple forums. The response from Apple when you call for support is that they don't support it because it's a Microsoft product. Why then do they offer the ability to sync your Outlook contacts for your iPod then, I ask?
So, the simple fix, you ask? Reset your iPod prior to syncing with iTunes. This will ensure that your Outlook contacts are updated and available on your iPod. You have to do this every time prior to plugging in your iPod to your PC. I manually manage my music and videos in iTunes, but if you store photos and want to be able to access your Outlook contacts on your device, they will sync automatically. When you plug in your iPod after the reset, Outlook will open. Don't close the program until after you're done doing any updates and eject your iPod.
That's it. :)
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