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Great article Damon, it is amazingly durable that 44 minute format isn't it? Half the length of most movies but the right album can take you twice as far!

Now, to be really annoyingly nerdy I wonder if you can tell me what the solution was to your iPhone music shuffling the artwork? Embarrassingly Adele 21 is the cover of half my collection! How dare she claim the work of Cream's Disraeli Gears and St Vincent's Daddy's Home!

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Omg such validation! Apple had me thinking it was just me, or that maybe I was simply insane. Here is what finally worked, I hope it does for you too:

- On the iPhone, Settings - Music - Downloaded Music - Edit - DELETE ALL SONGS

- Then synch to Mac...

Note: it took me more than one try to get the iPhone to actually delete all songs, it seemed to do almost all but not all at once. Just repeat the steps above.

I still have no idea why synch didn't work directly from Mac without this additional step on the iPhone itself. I believe this is a bug in Music that Apple hasn't fixed/doesn't care to. Cause they have given up on the album...? Wouldn't be the first time!

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Thank you! - I have tried that before but maybe a double delete is better, if not I might wipe the whole phone. I think Apple have given up on the album and the idea that we should own music - they want us to stream it all.

When I was a kid a friend had a portable record player ...now there's an idea!

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Ok one other thing to try if you haven’t yet: purge the user cache in Music, which seems to be in a folder still labeled iTunes. I use a maintenance program called CleanMyMac that found that for me during a “system junk” scan. I lost a number of album images in the process, which I had to manually replace. But among them, I suspect significantly, were ones that had been randomly assigned to the wrong albums!

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I came here specifically to ask how you fixed the album art kerfuffle - it's driving me bonkers! I worked hard to make iTunes artwork perfect on my computer and my iPhone destroyed all my toil. Will try these fixes...

While I'm here, LP lengths aside, I'll say this: if you don't play Willie's Red Headed Stranger in order, it really messes up the narrative and vision.

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I had the exact same album art problem, but only with cd rips and/or audio files that I had manually set the album art. I didn’t have to delete and reload everything on my iPhone. I noticed that if any audio file had a large image file used for the artwork, then it might cause a problem. So I took the image file for the album art, used photo software to convert to a lower overall quality (but still good image quality and high enough resolution) jpg file that was smaller in size. Then used the smaller file for the album art. So if an album art file was 500 kb (or larger) in size, it got reduced to ~100 kb or less, and it got imported to Apple Music without issue. It may not be foolproof, but seems to work so far. Also in iTunes/Music, I do not let Apple to automatically set album art, I have always had that setting turned off, and I do manual sync with music files.

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