I have a PC and recently upgraded to an Iphone14. Moving my music has been a huge cluster. Songs show up with the wrong album cover and lots of songs won't transfer over. I either get the circle indicating itunes can't find the song, or I get an error that it can't play a song in my region.
I purchase most new music through amazon, song I bought a few weeks ago get the region error or just won't transfer to itunes. I wonder if apple just wants to make it harder to load songs from another vendor. I ended up wiping out my entire library and reloading everything. That fixed 95% of the problems. I still end up with some missing songs that just won't load. Also, every time I hook up my phone, it duplicates the playlists so instead of 2, I have 4. Then 8. So I have to manually delete the duplicate playlists. You also have to do that through Itunes, because if I manually delete a playlist on my phone, the next time I sync, all playlists are gone.
Pain in the ass.
Anyone notice that if made playlists in the AmazonMusic app and ask your echo dot to shuffle your music, it will always shuffle the same 20 songs first, even though I have about 24 hours of music in my playlist. I assume they want you purchasing their streaming service instead of using your own playlists.