Behind the Eye: Upgrading iTunes Library to DRM Free is Not So Easy

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COLUMN: Well, I took the plunge this week and decided to upgrade about 50 or so albums in my iTunes library to the updated “DRM Free” option now offered by Apple for many popular albums/songs found in their store. Unfortunately, this has turned into one of the worst ecommerce experiences with Apple outside of an exploding MacBook battery.

Since I was setting up a new 2TB RAID array (1TBx2 “mirrored”) to move my library to from the old, and now full, 1TB RAID (500GBx2 “mirrored”), I thought it best to update the albums on my original drive to make sure they were all “good” before moving them to the new replacement storage device. While Apple’s “come on” in the iTunes Store made it attractive, the actual procedure proved anything but simple, or fun.

DRM free or pain in the buttThe come-on is pretty fair, an offer to upgrade my entire music library of previously purchased music now available on “iTunes Plus.” The cost is $0.30 a song, and 30 percent of the current album price, and $0.60 per music video (remember some albums on iTunes came with a music video, sometimes as a pre-order special).

Basically, when you login to the store, you will find an option in the right account box to upgrade to DRM-free music. The system looks at your library and past purchases and presents a summary of total songs, the songs purchased individually (i.e., singles), and albums. A big round button “BUY ALL” entices you with the total dollar amount to just do it.

Once I decided to “buy all” is where the adventure began. For the past three days I tried doing just that, only to get an email from the iTunes Store saying the system was unable to complete the purchase because one song/album could not be upgraded, and I should go back to the upgrade page and would now be able to buy the DRM free versions. Unfortunately, when I would go back and hit the buy all again, nothing would happen.

So, finally, today I thought “what the hell” and decided to try upgrading individual albums from the list provided on my personalized upgrade page, perhaps I would find the problem album (the store, sadly, doesn’t provide any feedback such as “here is the album you cannot upgrade, click to remove from your list”). I got through about ten, when I hit a problem again: apparently a Michael Penn album was “no longer available for upgrade and may be available in another part of the store.” After a moment the screen refreshed once the pop-up went away, and the album was no longer there. About halfway through the download of the first ten albums, I got a “timeout” error from the iTunes store, and then later an error saying “credit card processing is unavailable, try again later.” Then on the next batch of upgrades, I got an “the iTunes store is unavailable.” The latest error I just got (while writing this), is “Could not purchase ‘iTunes Plus Upgrade’. The network connection timed out” “of course, I have a home office with the fastest available hard-wired FIOS broadband connection, and so the timeout is entirely on their side of the stream.

I can only conclude that either a LOT of people are switching to DRM-free, or that Apple’s store is not keeping up with the growth in providing music, iPhone apps, video rentals, and the like.

Is it worth the hassle? Well, I can hear the difference in quality, particularly in some of the older albums I purchased on iTunes years ago. And being able to copy them onto whatever media device I happen to be using (I have about five iPods, a PSP, a Samsung device, a cellphone, a Yamaha recorder, a notebook, etc.) will be nice. This makes having to worry about running out of computer authorizations for my purchased music/videos an unnecessary worry.

Of course, I have to be able to actually get all the DRM-free albums. Sigh. I just tried again to do the “buy all” to save from manually clicking another 25 albums, but keep getting the “timeout” error. Doh.

I waited a bit and tried again, and on the next attempt I got another popup saying my purchase for “all” items had already been placed and to log into my account. No email confirmation, no alert. Whoa. Okay, so I logged into my account (click your email top right of iTunes store), and then there was a new box at top “You currently have items available for download to iTunes. 351 items. Download now.” Okay. Clicked the download, and it started. Finally.

While I love Apple, this has to be the most non-intuitive and painful process in buying anything from them EVER. Where’s the Genius Bar when you need it.

About Christopher Simmons

Christopher Simmons has been writing about music since 1984 when he sold his first feature to Polyphony (now Electronic Musician) magazine. He has composed music for two TV cable shows, is a member of ASCAP and PRSA, and is the managing editor for Music Industry Newswire(TM), as well as the CEO of Neotrope(R) Entertainment. His 80s music can be found on iTunes, Amazon, and CDBaby, among others. He played in several electronica bands in the '80s, and currently tries to find time to play with his studio gear. He is also an award winning graphic designer, photographer, author of one book "Fractopia," and has created digital art for numerous national magazines. © Christopher Laird Simmons. More at: .

3 Responses to Behind the Eye: Upgrading iTunes Library to DRM Free is Not So Easy

  1. Joe Fri, 06 Feb 2009 at 01:38:29 -0500 EST #

    No offense, and I understand that downloading fifty albums one at a time would be a major headache but trying to do twenty five and then ten?

    Why not try one, then two, then four until you find a reasonable number that could be downloaded at a time?


  2. admin Fri, 06 Feb 2009 at 01:50:41 -0500 EST #

    The author replies to comment from “Joe”

    Hi, Joe – the issue I (and others) have been having is that the iTunes store has a big button “buy all” which is supposed to save you going through 5-10 pages and pushing the buy button for individual albums one at a time. And everytime you buy one there is a popup confirmation. Unless one is no longer available between the time it shows it to you and the time you get to pushing the button! As noted in the story, I did end up having to push the buy button for individual albums ONE at a time as that was the only way it would work due to a major bug in their system in listing albums previously purchased as “upgradeable” when they are not. So, I did end up buying about 20 by hand, one at a time. Then I managed to do the “buy all” – but it’s been timing out during the download on the final 71 songs – basically a never ending rotating arrow (going on two hours now) with no further progress or any way to stop it. Hitting “pause” on the downloads page does nothing. In any event, the main problem appears to be with that one Michael Penn album, which “killed” itself once I tried to buy it alone.

    So serious issues:
    1) bug in system adding invalid albums to the buy all, listing
    2) inability to process credit cards due to system overload
    3) inability to consistently download tracks purchased
    4) system has permanently hung with no progress for 2 hours, and no option to clear/restart without hard-exit of program
    5) in restarting iTunes, it now says I have 172 downloads left needing to be downloaded; but it has already timed out on trying to download the first three. SHEESH.

    I just restarted again, and “unchecked” the box for “allow simultaneous downloads” — this seems to help, at least I think it does. We’ll see how long it takes now.

    On a more positive note, I had some custom hardbound books printed from iPhoto … superb. And don’t get me wrong, I’ve been using iTunes since before the software was renamed iTunes, so not going anywhere, but kind of miffed this has been such a chore. For this kind of service to compete with the freeloaders grabbing free/pir8 stuff off the web via the evil p2p stuff, this whole thing has got to work better. Luckily these are upgrades, so once it’s done, it’s done. Technology, gotta live it!


  3. Rebecca Fri, 13 Feb 2009 at 23:02:20 -0500 EST #

    Just a tip, iTunes gave the labels a deadline of April 1st to re-submit their full catalogs as DRM-free. So even when April 1 comes around, all the labels probably won’t have all of their albums enabled as DRM-free. I’d give it AT LEAST until May to be able to upgrade your whole collection without problems.