This past weekend I finally decided to sign up for iTunes Match. The promise of syncing my music and playlists in the cloud and getting some valuable space reclaimed from my iPhone and iPad became quite appealing.

Easier said than done. If you start doing a Google search for iTunes Match the first suggested autocomplete entry is in fact iTunes Match Sucks. I assure you it in fact does not suck, however the initial setup… well let’s just say it’s not exactly a pleasant experience.

If you’re lucky you’ll subscribe, turn iTunes Match on within iTunes and depending on the size of your iTunes library a few hours later you’re done. For many, and in my inner circle, the majority it hangs during it’s 3 step process.

For me it would hang at one of the first two steps. During my weekend of googling for solutions the most common ones included:

• Turn iTunes Match off and on again
• Turn iTunes Match off, update Genius and then turn Match on and retry
• Deauthorize you Mac from iTunes and reauthorize… retry
• While its hung turn off your WiFi / Internet connection and turn it back on
• While its hung inspect the open files attached to the iTunes process from within Activity Monitor to see which song it may be hung on and delete that song, retry
• Wait overnight… some have had to let it run for up to 4 days to complete

All seemed very promising and have worked for many but alas not for me. Toward the end of Sunday evening I contemplated calling Apple support and if they couldn’t resolve then cancel and try and get a refund but I just wasn’t ready yet.

Then I tried something that I haven’t read about anywhere and hence the motivation for this post.

I quit iTunes and proceeded to delete everything in the iTunes cache folder located here:

~/Library/Caches/com.apple.iTunes

I fired iTunes back up and gave it another whirl. All three steps completed within 15 minutes. I then turned on iTunes Match on my iOS devices and had everything synced and running perfectly within minutes.

It really does work quite well but a very frustrating uphill climb to get there. If you’re at your wits end I’d give the above a shot but please backup your cache folder first and don’t hold me responsible if your iTunes library get’s wiped out! It shouldn’t but my disclaimer nonetheless.

Good luck. It’s worth the troubles.