iTunes Match not playing all synced music.

I have iTunes Match subscription and have synced my personal music and playlists from my laptop, but only some of the songs from the playlist will play on my iPhone or iPad. The ones skipped are saying that it cannot find the file. However, I just subscribed to Apple Music trial, and guess what…all those songs now play without any new sync. Apple advertises that iTunes Match will play your personal music even if it can’t find it in the current Apple library. (I have music from ages ago that can’t be found anywhere now.) So, is this false advertising or a bug? Why should I pay monthly for Apple Music to play my own music? It’s barely feasible to pay annually for iTunes Match, since I used to be able to sync playlists via iTunes just a few years ago for free. I do like having the music in the cloud instead of stored on the device, but it does store the file on the device when it is played but I can delete those periodically. Any ideas how to get iTunes Match to play ALL songs?

Posted on Dec 19, 2025 6:59 PM

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iTunes Match not playing all synced music.

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