If you have this

and this

then you will need this:

Just don’t try to get it from here as you are required to make a “donation” to get it. Last time I checked donation implied voluntarily.

Of course iTunes will not work on Windows 98 but there are other free and better alternatives you can find on the internet, like YamiPod and EphPod.

So after spending over two hours searching for and downloading the drivers, trying to install and replace the existing USB drivers by trial and error, and we all know how “plug and play” Windows 98 is, the two devices could finally communicate. But what was fun was seeing how the once completely unresponsive iPod when plugged in slowly became more connected in stages.

At first we couldn’t even get the iPod to charge. Rewiring the USB connections and installing some other drivers got enough power to get the iPod to its charging state with the battery icon. More driver replacing brought it to the “Do not disconnect” state with Windows detecting a new hardware but refusing to install the iPod drivers. Manual intervention was required to replace the existing driver.

Finally “Apple iPod” and “USB Mass Storage Device” appeared on the Device Manager and all is well. Why must they make something so simple so hard?