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Hey ThomasbrthIt, Have you tried connecting with your computer and resyncing? Generally work's for me. Good luck. Cheers.

Most users report that resyncing does not work but this usually dos.

- Unsync/delete all music and resync

To delete all music go to Settings>General>Usage>Storage>Music>Tap edit in upper right and then tap the minus sign by All Music

Then as necessary:

- Reset all settings

Go to Settings > General > Reset and tap Reset All Settings.

All your preferences and settings are reset. Information (such as contacts and calendars) and media (such as songs and videos) aren’t affected.

- Restore from backup. See:

iOS: Back up and restore your iOS device with iCloud or iTunes

- Restore to factory settings/new iOS device.

Hey ThomasbrthIt, It's up to you, just how annoying is it for you? If simply re-syncing or deleting all music and syncing or Resetting All Settings did not correct, then Restore is your last option. Just make sure you fully backup the iPod to your computer before you restore so you don/t loose data / information. I'm visually orientated so I would restore, but that's just me. Restoring is a pain, but it generally fixes all ills. Good luck. Cheers.

Hey ThomasbrthIt, Hello again. You restored and it does nothing? It bricked on you? Or do you mean the artwork is still missing? If the latter, which restore did you do? Restore from Backup or Restore to New-- (a factory reset, like it comes out of the box, when you first bought it). If you did a Restore from Backup, and it did not work, then try a Restore to New. Just make sure you have backup this iPod to your computer first. Use the cable not the cloud. (I always had better luck physically connecting with computer when restoring). After the restore has finished add back your stuff from the copies on your computer. Good luck. Cheers.

Hey ThomsbrthIt, A while back, I had something like your issue. Artwork disappearing, only it started to cascade-- every album I tried to play would loose it's artwork and then would not play. A full restore to new was the only thing that solved it. It should work for you too! I'm sorry I hadn't remembered it when I first responded to your post-- could have saved you some time. I still have artwork drop out now and then, oddly it's always music purchased from iTunes never the stuff I downloaded from CD's and a simple re-sync has been working to correct, even though it doesn't always for everyone, it does work for me, (go figure.) Good luck. Cheers.

Are you sure 4008 is the error number?

It is not listed

Resolve iOS update and restore errors

and Googling only showed one hit and that said to download a program

Hey ThomasbrthIt, Ho No! found this on Wiki Errors, hopefully it helps, it's all I got, but error 4008 appears to be a Windows thing.

http://www.wiki-errors.com/err.php?wiki=4008

Good Luck. Cheers.