Always update your iPod with the latest software before troubleshooting.
iPod's skip protection works best with compressed audio files. This allows multiple songs to fit into iPod's memory cache.
If your audio files are large, or are uncompressed (such as songs in AIFF format), you may want to compress them, and use the MP3 or AAC compressors when importing new songs. Consider breaking large files into smaller files. If your songs aren't compressed, in AIFF or WAV format, for example, they take up a lot more space. Instead of holding 25 minutes of music, the cache can only hold a few minutes. This means the hard drive has to work a lot harder to keep the cache full. Since it has to turn on a lot more often, the hard disk is more prone to be affected by movement as it loads the cache, and that could make a song skip. More hard drive access can also affect battery life.
iPod provides skip protection by playing music from its solid-state cache. When all the music stored in the cache has played, iPod's hard drive copies more music to the cache. Shaking iPod while the hard drive is copying music can cause songs to skip.
If just one song skips when you play it, it may be damaged.
If you have an iPod (with Dock Connector) model and you're using a Windows PC, unplug the USB cable from iPod, or turn off the EQ.
Resetting iPod can sometimes help. When you reset iPod all your songs and files are saved, but some customized settings may be lost.
If all the songs you play skip and their file sizes are small, you may need to restore iPod. Warning: The restore process cannot be undone. All the songs and files on your iPod will be deleted. Always keep a backup of your important files. Content in your iTunes Library will not be affected by restoring your iPod.
Important: iTunes software may be used to reproduce materials. It is licensed to you only for reproduction of non-copyrighted materials, materials in which you own the copyright, or materials you are authorized or legally permitted to reproduce. If you are uncertain about your right to copy any material you should contact your legal advisor.