I recently took out an iTunes Match subscription, which is unusual because I hate “the cloud”. Despite it being 2016, I spend a lot of my time in areas without a data connection (like mountains, or in the car) and so the idea of having everything on “the cloud” loses some sheen when it’s not accessible half the time.

However, with iTunes Match it’s possible to delete all of your music and then, instead of just listening via “the cloud”, re-download a higher-quality version from Apple instead. This new version is 256kbps AAC (DRM-free), so the plan only works if your existing music collection is lower quality than that. A lot of mine is, so the princely sum of £21.99 for an annual subscription seemed very good value (remember there’s no DRM, so you get to keep the music you’ve downloaded even if you cancel your iTunes Match subscription).

Last week I paid my money and left iTunes ‘matching’ my library overnight, then uploading all of the music it couldn’t find in it’s existing master library. After that I had presumed I’d be in a position to just re-download everything and be sitting pretty. Unfortunately it didn’t work out for two reasons…

1) iTunes doesn’t match everything
Obviously Apple doesn’t divulge the technical details about exactly what algorithms it uses to match songs from your library against its own library. Whatever it is, though, it doesn’t always work. For example, the album “Back in Black” by AC/DC has ten tracks. Of those, iTunes matched six of my tracks but classed the other four as ‘new’ and therefore uploaded them from my machine into iCloud. This is a common problem.

This means that if I delete the album and re-download it I’ll get six ‘matched’ tracks back in high-quality AAC, but four of them back at the same quality because the original source was me! It seems a bit ridiculous to have a complete mish-mash of different-quality tracks all on the same album, so this was the first point at which I considered that this might not work. As an aside, Back in Black has sold around 50 million copies, so I refuse to believe that I genuinely have four tracks in a form never-before seen by iTunes anywhere in the world.

2) You can’t control the download location or naming
I tested my master plan with a single track before I deleted my entire library, and discovered to my consternation that iTunes dumps the newly-downloaded high-quality AAC version in a location of its own choosing within the designated iTunes media folder. So my original low-quality MP3 started as:
/Users/Haydn/Music/A.F.I./The Art of Drowning/09 - The Days of the Phoenix.mp3
and the new file was:
/Users/Haydn/Music/iTunes/iTunes Media/Music/A.F.I_/The Art of Drowning/09 The Days of the Phoenix.m4a
A lot of people won’t be bothered by this, but it annoys me immensely. This is not least because I regularly copy my music to an SD card for use in my car, so losing control of the naming convention (and seeing the very first one include a seemingly-random underscore) is a real pain.

Anyway, that’s why I’ve decided not to bother carrying on with this particular project. I suspect that the vast majority of people will not be overly concerned by the above, but hopefully this will at least help inform someone so that they’re fully informed before they make the leap.