Warning: My old iPod Classic ate 400 songs after I plugged it into a new laptop
Heads up for anyone still running a 5th gen iPod Classic in 2024. I hooked mine up to my Windows 11 laptop last week to add some tracks, and iTunes decided 400 of my files were "not authorized" and wiped them off the device in about 90 seconds. No warning screen, no popup, just an empty playlist where 400 songs used to be. I tried syncing again and it wiped 200 more before I yanked the cable out, so now I've got a brick with 600 missing tracks. Turns out Apple dropped iPod support in iTunes long ago and the "authorization" thing is basically a dead end on newer machines. If you still have one of these, back up the files on a drive first and never let a new computer see it. Anyone found a workaround, like Rockbox or an old iTunes version on a spare PC?
That bit about iTunes wiping 200 more before you could yank the cable makes my stomach drop, seriously. Losing 600 songs off a device you trusted for years is just brutal, and the worst part is there was zero warning, it just did it. I had a 5th gen too and this exact fear is why mine has been sitting in a drawer untouched for like three years now. You're right that it's an authorization dead end, Apple basically gave up on these things and the software treats your own files like they belong to somebody else. Honestly your advice to back everything up on a drive first is the move, and if you do mess with it again, keep that iPod offline and use something like foobar2000 or an ancient iTunes on an old machine that never touches the internet. Really sorry this happened to your library, that hurts.