It appears to me this a site where we all post problems and not a sole really knows how to fix them, the sites that charge have very suspect t T & C for me to buying into that. I have had a similar problem for years and can't seem to get an answer of fix. Apples actual operational support is seriously flawed.
Unfortunately, this is not Apple Operatipon support, this is a iPod Classic community discussion forum, consisting of users like yourself, who had enough BS support from Apple, but shares our experience, with those who had similar iPod classic issues.
Some issues like this post may have been addressed, but under different header, so if you are lucky, some contributor finds you post not too hostile, and they respond or else you may have to search for you solution.
Here is a link to Apple support solution on soing skipping, not that it will help you.
here is an earlier post that solve the problem
If your music stopped halfway in iTunes, then redownload it again, it maybe corrupted, there is also a 3rd party apps MP3 validator, that correct MP3 songs with corrupted ID3 tagheaders.
Google MP3 validator, run it in your library.
Have a nice day!
All, I struggled with this issue too. After experimenting wtih several solutions, I finallly did the following and it worked after 5 or 6 tries. First, delete the problem child song from your music library. Second, go to iTunes store and find the problem child song and re-download it. ( you won't get charged....you'lll get a notification that you already purchased said problem child song, but just click ok). I had to do this 5 or 6 times. It continuously downloead only portions of the song....however after about 5 or 6 tries, tthe whole song ultimately downloaded. Sucess. Best of luck.
I suspect the inital spark for this thread was a slightly different problem, but for those having issues with recent purchases from the iTunes Store...
Assuming you are in a region where you are allowed to redownload your past music purchases, delete the broken tracks from your iTunes library, go to the iTunes Store home page, click the Purchased link from the Quick Links section in the right-hand column, then select Music and Not on this computer. You should find download links for your tracks there.
If you don't see them straight away it may help to close and restart iTunes.
While downloading select Downloads in the left-hand column and make sure Allow Simultaneous Downloads is unticked.
If the problem persists, or that facility is not yet available in your region, contact the iTunes Store support staff through the report a problem links in your account history, or via Contact Support.
See also: HT2519 - Downloading past purchases from the App Store, iBookstore, and iTunes Store