Why does my 1st gen. iPod shuffle have trouble syncing to iTunes 12.2.2.25 (I have a mac OS X 10.9.5)? It usually syncs fine for the first few minutes, but then it's like it loses connection.
Nothing I do stays after I disconnect the iPod. It'll act like it registers what I'm doing; if I delete a song, it'll delete from the playlist. But then, when I listen to my iPod, the song is still there and when I reconnect my iPod to iTunes, the song is still there. It's very frustrating; I keep having to disconnect and reconnect my iPod to get anything done. I sometimes get an error message saying it cannot find the device, but not always.
iMac (21.5-inch, Late 2013), OS X Mavericks (10.9.5)
