How to put an iPod Classic into Debug mode

Hold down the Center and Menu buttons until the iPod restarts.

Or if your Pod is dead, plug it in and flip the Hold Switch located on top of it in the unlocked position.

When you do this, holding the Center and Menu button is important to remember to restart into the Stock iPod OS.

Hold down Previous Track and Center button.

Now, the screen should become the Apple Logo, and once the screen turns white, it is safe to release the two buttons.

Navigation of the Menu will help out with using the iPod to figure out it's problem.

Menu is to return to the previous screen, or go to the next screen in some of the different functions.

Center Button is to select a Menu line and enter that line's designated function.

Skip Track and Previous Track buttons are used to scroll through the lines.