iTunes Match Failed Me

Remember iTunes Match? It's great. But Apple stopped promoting it (probably rightly so) a couple years ago when they realized they could make more money charging $10/month for Apple Music than Match's $25/year.

Anyway, I loved it and still do. It uploads all of your digital music to Apple's cloud and makes it streamable on all of your devices. And I mean all of it – especially your ripped mp3s, live albums, or anything else not in the iTunes Store. And if they can "match" any of those unofficial mp3s to a song from the store, they'll "upgrade" you to the higher-quality AAC file for free. I had thousands of low quality mp3s ripped in the early 2000's and late 90's. Now they're metadata tagged appropriately, with artwork, and sound better.

When I first joined iTunes Match (seven?) years ago, I uploaded all my music, made a backup of my local library, deleted everything, and just streamed from then on to save hard drive space.

As I acquired new music, it went to Apple's cloud, but I never got around to backing it up offline.

As I've been writing about this month, I'm re-evaluating my backups strategy. This week I got around to looking at my music collection and decided it was time to retire that old external drive and put everything in B2 – around 300GB.

Knowing that drive was out of date, I figured I'd just download a fresh, complete copy from Apple.

I selected everything in iTunes, and clicked the download button. And waited.

The next morning I found my nearly 25,000 tracks stored locally – and a ton of errors.

Out of the 25,000, nearly 1,500 had failed to download and reported all sorts of various network errors.

I made a quick smart playlist showing all songs in the cloud but not available locally. This made it easy to isolate the problem items.

I tried downloading all the missing songs, but each one failed again. So I tried downloading a few individually with no luck. You can see where this is going.

After much testing and troubleshooting these 1,500 songs (all from various albums, some from ripped CD's, some purchased from the iTunes Store) are seemingly gone.

It's not the end of the world. If I really want some of them, I'm sure I could just re-purchase or stream from Apple Music. But others, especially some amazing live albums I collected in college are gone.

So I uploaded what I had to B2. And then made a csv export of the playlist of missing songs for good measure.

And while I love and take advantage of the cloud's convenience, this is why I don't trust my data to be in only one place. It's my fault for not backing up this part of my data if it was important to me. It's the first real data loss I've experienced in years – maybe since 2010. Maybe it's just a bug that Apple will eventually fix.

But I've learned my lesson.