The messy, the missing and the mistakes: Adventures in iTunes Plus upgrading

Well, it’s been almost two months since Apple announced the huge expansion of higher-quality and DRM-free music in its iTunes Store “Plus” offerings and I think it’s fair to say that the upgrade process is an unmitigated disaster. Despite personally paying 30 cents per track to upgrade hundreds of tracks, Apple has erased my metadata, forced me to spend many hours deleting duplicates and refused to even make available upgrades to some of my favorite albums, long after the “plus” versions showed up in the store at full price. And getting the upgraded files from my laptop, where I downloaded them, onto my desktop iMac has been another nine layers of hell. Shame on you, Apple. I’m calling it “The Messy, the missing and the mistakes.”

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A little background: Having previously spent a ton of dough in the iTunes store over the past five years buying music tracks that came encoded at only 128 kilobytes per second and locked up with Apple’s Fairplay DRM, I was willing, fortunately able and even a little excited to spend even more to get everything upgraded and unlocked. Apple’s “Plus” tracks, after all, come encoded at double the bit rate, noticeably improving sound quality, and without any DRM, freeing you to play the tracks over an assortment of cool gear like the Sonos or Logitech Squeezebox streaming systems or your Amazon Kindle, for example.

I started by making a smart playlist of all the songs in my library on my Macbook Pro. The smart playlist includes all songs encoded at a bitrate of 128 kbps and with the description “Protected AAC audio file.” Before buying any upgrades, the list included 868 files (some songs purchased over the past five years I’d subsequently deleted or replaced with higher-quality versions burned from CDs).

Just a few minutes after Apple announced the upgrade program, iTunes showed I could upgrade 294 songs. When I clicked to make the purchase, iTunes asked me if it could throw away the old files and I checked yes. A few days later, another 132 songs were available for upgrade. This time I did not get a check box asking me about whether to delete old files. So at this point, I had paid to upgrade some 426 tracks. But my smart playlist showed I still had 594 locked up songs — a drop of only 274 songs.

As I started to investigate that mystery, I realized that in hundreds of instances, iTunes had not automatically copied metadata like star ratings and play counts from my old tracks to my upgraded tracks and it had not gotten rid of the old tracks. My library was now littered with duplicates and many of my shiny new “Plus” files had no ratings, play counts or other data attached. Blech.

I emailed the iTunes store support several times and got a series of utterly useless responses which amounted to little more than “oops, sorry.”

The only fix — admittedly very labor intensive — is to start by doing a search for duplicate files in iTunes. Then, for each duplicate resulting from the messy Plus upgrades, delete the song LISTING for the new DRM-free file (it’s described as a “Purchased AAC Audio file”) and delete the UNDERLYING ACTUAL FILE of the older, DRM-locked file (it ends with a three-letter extension of m4p). Then go back into iTunes and click on the remaining prior listing for the song, the one with all your metadata. iTunes will say it can’t find the file and lets you choose to link it to a new file. Navigate through to the new DRM-free file and select it. Yes, Virginia, you have to do this one by one for every messed up file. UUUGGGGHHHHH!

Another partial fix, which you have to do every time BEFORE you plan to purchase upgrades for a bunch of songs, is to go into your iTunes store account info. Near the bottom of the account info screen is a line that says “Reset all warnings for buying and downloading music.” Click on the button that says “Reset Warnings.” After you do this, on your next upgrade, iTunes will re-ask if you want to delete old files when you do a Plus upgrade and that seems to avoid much of the mess.

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Once you’ve dealt with the messy and the mistakes, you’re left with the bizarre-o world problem that Apple and the record companies seem to be leaving out upgrades on many albums that are already for sale in Plus versions at full price.

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For example, I purchased from the iTunes store a couple of albums by the White Stripes. Both albums are shown as currently available for sale in Plus versions but I’ve never been offered an upgrade. Again, an email to iTunes store support came back with nothing. Apple – I want to pay you money and you won’t take it! Not smart.

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The final disastrous blunder is the mess resulting from my keeping a copy of my music library on my iMac as well as on my Macbook Pro. As you’ll remember from the original days of the iTunes Store, you can authorize up to five computers to play your purchased, DRM-locked music tracks. So I have a near-duplicate copy of my library on my iMac. But I upgraded all my music to “Plus” versions on my laptop. Apple has offered no way to sync the libraries and my workaround is so hellish I almost can’t bear to mention it.

I printed out the smart playlist of old, DRM-locked files on each computer. One list was about 10 pages, the other six pages. Then I laboriously compared — line by line — every file that was off the laptop list (because it had been upgraded) but was still on the desktop list. For all of those files, I deleted the LIBRARY LISTING AND THE UNDERLYING ACTUAL FILE from my desktop’s hard drive. Then I used the program Syncopation to sync the two libraries. It copied over the new unlocked “Plus” files with their correct library listings from the laptop. Phew!

None of this is user-friendly or customer-friendly or even very nice. Apple needs to overhaul the “Plus” upgrade program and quick. And the company really should be more responsive to complaints about the currently broken system.

UPDATE: I see over at jkOnTheRun (via the always handy Macsurfer site), that the 30 cents per track fee is also infuriating some customers.

Comments

10 responses to “The messy, the missing and the mistakes: Adventures in iTunes Plus upgrading”

  1. AdamC Avatar
    AdamC

    I didn't know Apple users are so hard to please, when things didn't work right they will try to get as much attention as they can by blogging. Sad in these very difficult times, people are losing their jobs and we have this kind of user telling the whole world how rich he is and he has load so f money to spend but when he didn't get any attention from Apple it made him fuming mad and started saying nasty things about Apple. Sad

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  5. murphy_mac Avatar
    murphy_mac

    This is definitely a mess. On the computer where I did the download the new songs replaced the old and got the transferred meta-data.

    But I have another machine with its own library. I don't know what I'm going to do about getting the songs over there, but I suspect it'll be messy and semi-manual. With no way to update the metadata.

    It would be nice if the new sharing features in iTunes 9 dealt with this, but I haven't checked that yet.

  6. ampressman Avatar

    Yeah, I haven't read anywhere how the home sharing treats metadata.
    But it sounds like it's for copying brand new songs, really, so it
    probably either brings along nothing or whatever ratings etc existed
    on the original track. I'd be surprised if it's more intelligent than
    that.

  7. ampressman Avatar

    Yeah, I haven't read anywhere how the home sharing treats metadata.
    But it sounds like it's for copying brand new songs, really, so it
    probably either brings along nothing or whatever ratings etc existed
    on the original track. I'd be surprised if it's more intelligent than
    that.

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  9. CD Printers Avatar

    I do agree with this.

  10. […] Eventually, the music industry saw the light, thanks in part to Apple agreeing to a huge price hike, and stopped requiring DRM encumbrances. That was a great move but it left a lot of us with collections filled with previously legally purchased music that still had the DRM lockdown. Apple graciously offered to upgrade such tracks to a higher quality, DRM-free version for 30 cents a pop. But the iTunes Plus upgrade service, as it was called, was a disastrous mess. […]

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