iTunes Match: the shade of Steve Jobs will be steaming

The introduction of iTunes Match seems like an even bigger cock-up than the introduction of MobileMe – in the UK, at least, which is all I can talk about.

I’ve been an iTunes user for a long time – probably since near the beginning of iTunes on Windows. I was seduced by the iPod and further motivated by running out of storage space for my collection of CDs, which must have been around 1,000-strong by that time. Not a huge collection by some standards, but taking up too much square footage on my office wall. So I ripped ’em and became a slave to the instant gratification of the Buy button.

Match seemed like a no brainer: all music available everywhere, 256 Kbps DRM-free versions and an effective back-up in the cloud. And to be fair, all these things may prove to be true. But three days in, I’m still trying to get my iTunes library matched and sync’d.

After two or three betas, the nightmare of getting everything set up seems incredible. I would have expected Apple to have resolved most of the shit by now. Signing up was bad; it took several attempts to complete the process. Having done that, signing on to iTunes was screwed for, maybe, 15 or 18 hours, because valid user IDs and passwords were rejected. The popular theory was that the Apple’s servers were blitzed. This was a cause of major panic until I realised it wasn’t just me.

Having got past the first hurdle, there are three further steps for iTunes Match: collect information about the library, match tracks against the iTunes catalogue, upload any tracks that couldn’t be matched. The fun really begins here: I have lost count of how many times iTunes has hung during the first two steps. And it is not just iTunes, but the entire machine that locks, requiring a power off-on cycle. This is more of a pain than usual because it’s necessary to watch the restart and catch iTunes to either stop the current step or force-quit the application; otherwise the current Match step would continue and almost immediately the app would hang again.

Of course, every restart of Match begins again at the beginning. And with over 18,000 items to process, this takes a while. Checking on the Apple user forums, I discover that Match tags some tracks with “error” as the iCloud status. It is these errors that cause the hangs. The workaround is to delete and trash the tracks from the catalogue. The deleted tracks can be recovered from trash; so in theory, nothing is lost – but I have yet to confirm that these tracks can be safely reintroduced.

This is major pain, made even worse because not all errors are identified on the first pass. Multiple iterations of steps 1-2-hang-restart-interrupt-delete tracks-recover from trash-start Match are needed. Eventually, I get to the point where Step 3 starts to upload unmatched tracks. But this doesn’t mean an end to the grief because the upload process – some 5,000 tracks to go – hangs as well before more than a few percent have been processed. I’ve now got the stage of of stopping the upload after 200ish tracks, so I can quit iTunes correctly to “bank” the work. I’m still going through this loop with 2,300 tracks remaining.

It’s reported that Steve Jobs was incandescent with rage after the initial embarrassment of MobileMe. Frankly, this seems an even bigger fiasco. I hope it’s not indicative of complacency from Apple.

If you haven’t yet signed up for iTunes Match, my advice is to wait: first, to let the immediate rush pass and secondly, hopefully Apple will make some improvements. In the meantime, here are three links that I have found helpful in addition to the Apple user forums.

Bugs & Fixes: Three essential iTunes Match troubleshooting tips

iTunes Match: What You Need To Know

How to upgrade tracks to iTunes Match, fast

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