Issues with Music Cloud Library and "damaged" uploaded MP3s

TidBITS Talk
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TL;DR: Music that used to play on my iPhone doesn’t play anymore.

I have a pretty large music library of mixed sources, which dates back to SoundJam. I subscribed to Apple Match when that became available, then iCloud Music.

I have sporadically noticed that when I try to play some of my songs on my iPhone, iOS/Music pops up an error reading “Cannot Open / This media may be damaged.” If I find that track on my iMac, MacOS/Music plays the song with no issues. (I usually shuffle playlists, so iOS/Music just silently skips over these “damaged” tracks, which serves to conceal the problem.)

Recently, I’ve tried to track down the source of this. It appears that the problematic songs are all of type MP3, and cloud status Uploaded. There are about 3000 of these songs, so correcting the issue one-by-one is not a good option.

I experimented by using MacOS/Music to convert a single track to AAC, deleting the original track from the Library, and waiting, and sure enough, the new track will show up and play correctly on my iPhone.

I then tried to convert two albums the same way, but before I could delete the original tracks, the new tracks had been marked with the cloud status Duplicate. I deleted the originals nonetheless, but now those tracks are not even showing on my iPhone. File > Library > Update Cloud Library does not help.

I thought that Doug’s Applescripts might have a solution for me, but his Convert & Replace script is so clever that MacOS/Music doesn’t notice that the track has changed, so the new version does not upload to the cloud.

As an additional complication, I don’t want to lose the manual playlists that I’ve created. Doug’s script preserves the songs in the playlists, but as I said, doesn’t fix the issue on my iPhone.

Does anyone have a suggestion as to where I can go from here?

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So, I did it the hard way.

I went to each playlist, found the tracks that were MP3/Uploaded, right-clicked > Show in Playlist for each one to see if they were also in any other playlists, and made notes of that.

I dragged these tracks out of Music into a new folder.

In Music, I right-clicked > Remove from Library.

In the Finder, I converted the tracks to AAC using the app XLD, dragged the converted files into Music, and manually added them back to the appropriate playlists. Cloud then accepted the new versions, and now they play on my iPhone.

After I went through all of the important playlists, I made a smart playlist to find the remaining MP3/Uploaded tracks and converted them as well.

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Is there a reason you did not use the Music programs’ Convert? Is XLD a terminal type program, or can someone without programming skills use it? I run into the problem of soooo many errors when I try to sync my phone to my playlists with a physical connection. When I turn on Sync, I seem to get duplicate lists (the Name 1 phenomenon) and all songs do not sync. This will be a slog, but want to clean things up once and for a while.

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Tried it out and looks nice and simple

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If you convert within Music, the MP3 remains with ‘Uploaded’ status, and the new AAC is marked as ‘Duplicate’. Deleting the MP3 does not cause the AAC to be reuploaded to the Cloud.

Looks like you already found XLD, but for the help of others, the App is X Lossless Decoder: Lossless audio decoder for Mac OS X.

I notice that you mentioned the Playlist1 issue. I had this as well. DO NOT DELETE EITHER PLAYLIST. I deleted the Playlist1, and when I came back the next day, BOTH playlists were gone. I’m thinking that if you create a new playlist and copy the contents from the old one to the new one, that will allow you to delete both Playlist and Playlist1 safely.

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I’ve recommended XLD in other threads as it can do batch conversions and also has a Secure CD ripper which compares your rip to others in the database so you can see if it’s an accurate rip. Music and iTunes does not have that and some CD’s appear to rip correctly until you play the files and realize that there is a problem. It also let’s you specify where you want the files to go where iTunes/Music puts the results of conversions in the same media folder as I recall. Since I like to keep my various conversions separate such as AIFF, mp3, and ALAC, I want each on a separate drive not all in the media folder.

I don’t use iCloud so I can’t say how adding these files to your Music database will affect that.

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