I heard about this little hack that will upgrade old low quality MP3s you might have hanging around your iTunes library and thought I’d give it a shot. Basically iTunes Match gives you access to any song you have in your library, from any of your devices. It can do this because they have a huge archive of songs and just match up song titles, the trick is that all the files they have are in 256 kbps quality.

Since files in my library range from FLAC quality with upwards of 1000 kpbs all the way down to 96 kbps files I’ve had forever I thought this might be a great opportunity to beef up some of the lower quality ones.

So this is the thing. I have my home iTunes library. I buy a year of Match for $20. iTunes scans my library and matches it with the files they have. So then, say, from my other laptop or my iPhone, I can listen to any song I have at home by downloading it from iTunes on the fly – which iTunes will let me do now that they know I have it already. Now there’s no requirement to keep your old files. You could trash them all if you wanted to, and then just download things as you go, but anything you have at higher bitrates would be reduced to 256 -and I wouldn’t recommend trusting a single service for that anyway. But the same is true for the lower quality songs, when you redownload them, they are at 256.

So, now that everything is matched, you can create a smart playlist that looks for music files with a bitrate lower than 256 where the iCloud status is matched or purchased. Then delete those files from your computer (not from iCloud!) – and then, just select all, and redownload them.

It sounds pretty easy, and it kind of is, but it kind of isn’t too. Make sure you read that how-to I linked to earlier in depth, 2 or 3 times. I have over 20,000 songs in my iTunes and over 8,000 of those matched this criteria and downloading that many files doesn’t happen quickly, or flawlessly. I ran through these steps and while it mostly worked, I got “can not be downloaded” errors on about 3,000 songs. To which I was like WTF?! So then I had to sort my library by iCloud status and then selected the ones that weren’t downloaded and tried to download them. Again, it sort of worked, but about 1,300 still had the “can’t download error” -tried it again, it got more, but still threw the error on about 400. I’m in the process of grabbing those now. So it’s not that the song can’t be downloaded, it’s that there’s some conflict that prevents it from happening on the first try. And sometimes the 2nd. So it was a bit of a pain, but in the end it’s not too bad of a deal.

Once I finished all this I updated all my backups. I have a Time Machine backup drive with a partition that keeps a copy of my iTunes library for my Sonos system to work off of. I also have Amazon Cloud player and Google Music. So again, syncing to all these places takes some time, but now I have all those files everywhere and I’m pretty confident I can listen to pretty much anything anywhere.