If certain songs or audiobooks won’t play on your iPod, here are some things you can try to resolve the issue.

iPod shuffle can support a variety of audio formats. Here’s a list of compatible and incompatible formats. For other iPod model audio formats, click here.

When syncing Contacts or Calendars from MobileMe, an iPhone, or an iPod touch, to Outlook 2003 or Outlook 2007, changes that have been synced to your computer may not appear in Outlook even after the sync has been completed.

This document is for Windows XP. Click the appropriate link below if you have a different operating system.
Windows Vista     Mac OS X
 
When the iPhone or iPod touch is connected to Windows XP, a dialog is presented with choices for connecting as a digital camera and working with the digital pictures stored on the device.
This is the default behavior under Windows XP for digital imaging devices. Windows provides a way to disable this notification on a per-device basis.

This document explains why iTunes or the operating system may indicate that iPod’s disk is full when it doesn’t look full.

There is no available space on iPod’s hard disk when it is used as an external FireWire or USB hard drive, yet the disk looks like it is empty or only has a few files on it.
iTunes cannot copy any songs to iPod even though it says the music library is less the size of iPod’s hard disk.