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AndersHG : you need 1st to switch Go online in playback ... then wait to sync and then again switch offline to work 🙂
try it !
do you have your playlist in offline mode?
add a new song to that playlist.. then in setting > playback > switch to online for add that new song...(that is sync) then switch again on offline at the end of that sync.
all your list most work now with cover art in offline mode
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yes add new songs and resync... after works delete any song you want. 🙂
size is not the problem i can have 3333 songs.
what device u use? iphone? what is ur iOS version?