My iPod Classic 160GB won't sync new TV shows

My iPod Classic has never had any issues, and I've got some purchased TV shows on the device but for some reason the new shows that I have downloaded won't sync (specifically Rick & Morty season 2). iTunes says that they can't sync the episodes. Any answers on this? I'm guessing it's Apple making it so that new shows can't transfer and we are forced to buy another device... Not happy. Any advice would be great. Thanks.