Why My Click Wheel iPod classic Won't Connect to iTunes

iPod classic is a drive-based MP3 player. Differing from other iPod models, this series doesn't require Apple Mobile Device USB Driver to connect to your computer. So when you found somehow your iPod classic won't connect to the iTunes, uninstalling and reinstalling iTunes probably cannot solve the problem. Below are some suggestions for you.

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Before Starting, Please Try below Troubleshooting Tips

• Please check if your USB cable is working properly. And it wouldn't hurt to also try a different USB cable to rule out a faulty/damaged cable.
• Please check if you can find your iPod on Windows Explorer, like:
  

Reset Your iPod

Most of problems with iPod will be solved by resetting it. To reset an iPod, you can:

• Connect iPod to a power outlet using the iPod Power Adapter;
• Toggle the Hold switch on and off (set it to Hold, then turn it off again);
• Press and hold the Select and Menu buttons for at least 6 seconds, until the Apple logo appears.

For a complete guide, please refer to this How to Reset an iPod article.

Putting iPod devices with a Click Wheel into Disk Mode

• Toggle the Hold switch on and off (set it to Hold, then turn it off again.)
• Press and hold the Menu and Select buttons for at least six seconds, until the Apple logo appears.
• When the Apple logo appears, release the Menu and Select buttons and immediately press and hold the Select and the Play/Pause buttons until the Disk Mode screen appears.
• 
• Connect the iPod to your computer; the screen on the iPod will should say "Do not disconnect".
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If you are having difficulty putting your iPod into Disk Mode, set it on a flat surface. Make sure that the finger pressing the Select button is not touching the Click Wheel. Also make sure that you are pressing the Play/Pause button toward the outside of the Click Wheel and not near the center. If you are still unable to put your iPod into Disk Mode, use one finger from one hand to press the Select button, and one finger from the other hand to press the Play/Pause button.