Original post by: Trumbit ,
Ok so here is how i *fixed* this problem in case anyone has the same problem in the future. iTunes 12.5.5 seems to have removed the ability for the old iPod classic to charge when not "connected" to your pc. It must have updated a few weeks ago without my knowledge and its this thats been tripping me up. Thinking back I don't think my classic was ever able to use an external usb charger (unless it was an official apple one) so this threw me also. Anyway I just uninstalled iTunes and installed the best version (imo) 12.3.1 and imported my library and BAM charging like normal again. What a complete PAIN, took me so long to figure out why this was happening.....