iTunes Plus: an upgrade odyssey

When I first heard the Macworld Expo 2009 announcement that Apple was going to fully DRM-free music on the iTunes Store, I was excited. I jumped at the chance to free my music from the shackles of oppressive copy protection.

The extra charge per song or album was a bit of a let down, but being a bleeding edge Machead the surcharge wasn't much of a shock and I just accepted it. However, the bad experience with iTunes Plus that followed was something I would never have expected.

The problems with the iTunes Plus upgrade process were many and varied so I broke them down into categories.

All or nothing The iTunes Plus Upgrade process doesn't allow the user to pick which tracks or albums they wish to upgrade. This really isn't a problem for me because I want to liberate all of my content.  But, say for instance, one night, a year ago in a drunken haze, I purchased a Tiffany song. I woke up the next morning and realized this atrocity through my hangover and deleted the song before anybody found out about it. Now, a year later, I perform my bulk iTunes Plus Upgrade. Gasp! Tiffany reappears in all of her 256 kbps sappiness.  That's right. The bulk upgrade process forces you to buy even songs you may have discarded. It's all of your purchase history or nothing.

Duplicate dilemma After performing an upgrade, I noticed a lot of songs in my collection were duplicated (both 128 bit and 256 bit versions coexisting). Yes, iTunes does provide a "Show Duplicates" menu item to help you find clones but it doesn't catch all of them. For example, some of the names of tracks have changed due to missing punctuation or different spellings causing "Show Duplicates" to fail.  The only way I could resolve this problem was by printing out my iTunes Plus Upgrade purchase history and checking each song via band name. It only took a hour and a half of my life and I think I may have did it correctly, maybe. I believe this error cropped up because Apple is using newer entries from the CDDB (Gracenote) then when the 128 bit versions were encoded and sold.

Apple thinks I've been naughty This was my favorite flub. The bulk process upgraded an album of mine from explicit lyrics to clean. Thank you, Apple. I know you are only looking out for my best interests, but I like the dirty words peppered throughout by glam metal music. I contacted iTunes support about this and all they could do was issue me a refund which I still haven't received. I purchased the explicit lyrics version of the album on eBay the next day for $5.00 and ripped it at 256 kbps. Bummer.

Upgrade? What upgrade? Quite a few of my purchased albums and tracks are now available in iTunes Plus format but don't show up as part of an upgrade. Once again, I contacted iTunes support. I provided examples of 8 albums that should appear in an upgrade but don't.  The support folks said that they have fixed the problem. I should re-login to iTunes and the upgrade option will appear. No dice. Nothing shows up as needing an upgrade. I was instructed on two occasions by iTunes Store support to attempt this procedure with the same results. It makes me wonder if they can actually fix these type of problems at all.

Customer disservice The support I received for the iTunes Plus upgrade process has been nothing short of abysmal.  I really hate to say it, being a loyal Apple customer for 20 years, but it's the truth. I've had three incidents in the first week alone (a new personal record). Furthermore, iTunes support would rather issue refunds than fix problems. Or when they actually endeavor to fix something, it's not properly addressed and the customer is left wondering what to do next. In fact, I don't even think they are reading their e-mails thoroughly. I had one incident where the customer service representative didn't even recognize that the affected order number was in the titles of the e-mail chain. If this is just a taste of what is to come in a post Jobs era, I fear for the future of Apple.

If you want to dig deeper, read the Apple Support forums and see more problems than just the ones I've described here.  I can only speak from my own personal experience.  And, I can provide one suggestion. Wait until at least April to upgrade your iTunes library. By then, the store transition should be complete and hopefully most of the kinks will be worked out. Hopefully.