"Cannot connect to iTunes, file missing"


New member
Just a heads up, I no longer have the device in question as I dispatched it in a fit of rage, but years later I just wanna know what was wrong with it so hopefully someone can help me out.

So I used to have an iPod Nano 4th Gen, and I had it for 4 months with no issues. Then one day out of nowhere, I tried to connect to iTunes and I got a message along the lines of "Cannot connect to iTunes, missing file" it may have quoted the file name but sadly I cannot recall it. So first I tried updating to iTunes 8 (the newest version at the time) and that did nothing. I tried resetting my iPod and that also did not work. I updated my software and again, nothing. I even tried to restore it, but it would only allow me to do so if it was connected to iTunes. (now do you see why I was so upset?) I finally ended up destroying it which I now realize was immature and silly, but I still would like to know (if at all possible) what actually happened and if there was something I could have done. Any help would be much appreciated.


Staff member
Back then it could have been complaining about not connecting to the store (a common error) and the error message was not interpreted completely, and it was the missing DLL problem. The fix for that is uninstall ALL Apple products (iTunes, Bonjour, Quicktime) download a new installer and reinstall iTunes. Most people forgot to uninstall Quicktime.

If it was actually complaining of connecting to the iPod, " iPod XXX Cannot be synced. The required file cannot be found" for example, then a file that you told it to sync was not available on your hard drive anymore (a common problem caused by people mucking with their music with Windows Explorer). Reconnecting the file in iTunes resolves the problem.

It is hard to pin point the issue from a partial error message from a previous version of iTunes (4 older than current) based on memory of the past.