I hit a very annoying issue using Audible.com on my Mac with iTunes and my iPhone. I thought I’d document it in case others hit it.
Setting the Stage
I got a MacBook Pro in early 2009. I buy audiobooks from Audible.com and store them in iTunes. From iTunes I sync the audiobooks to my iPhone so that I can listen to them while driving, cleaning, etc. The audiobooks are DRM-protected (urgh), so the first time you try to play an audiobook in iTunes it asks you to enter your Audible user ID and password. It then validates your Audible user ID and password and verifies that you have purchased the audiobook file. Once you have authorized your Audible.com account in iTunes, you never have to enter your Audible.com user ID and password again. Also, once you have authorized your Audible.com account in iTunes, you can sync audiobooks to your iPhone.
The Symptoms
Recently IBM got me a new 2010 MacBook Pro for work (thanks IBM) so I gave my 2009 MacBook Pro to my wife. So that I wouldn’t have to set everything up from scratch, I backed up my entire 2009 MacBook Pro to an external drive using Time Machine and then restored this configuration onto the new MacBook Pro. After a couple of hours of data transfer both ways, my new MacBook Pro was a clone of my old MacBook Pro, or so I thought.
Unfortunately I realized quickly that something was wrong with my Audible.com audiobooks. The first symptom was that none of my Audible.com Audiobooks were on my iPhone. I tried to play one in iTunes and it asked me to authorize my Audible.com account. This was a surprise because I would have expected the Time Machine backup / restore to have made this unnecessary (since my iTunes configuration was already authorized), so I typed in my Audible.com user ID and password, hit sync, and sure enough the ebooks synced successfully to my iPhone.
Later that week I noticed that the audiobooks had disappeared from my iPhone again!
The Bug
To make a long story short (too late), after some experimentation and support discussion with Audible.com, I discovered the following steps to reproduce the problem.
- Start iTunes
- Double-click an Audible.com audiobook
- iTunes prompts you to authorize your computer for your Audible account by asking you to enter your Audible.com user ID and password
- Enter Audible.com user ID and password and successfully authorize
- Sync iPhone
- Audiobooks copy successfully
- Close and re-open iTunes
- Sync iPhone
- Books are deleted from iPhone
Basically anytime I closed iTunes, my Audible authorization was lost. This indicated that authorization was succeeding but was not being persisted to disk. I sent the steps to reproduce to Audible customer support.
The Solution
As I suspected, it was a persistence problem. The Audible support person pointed me to the file /Library/Preferences/com.audible.data.plist (a Mac property list file) where (apparently) the Audible / iTunes code persists your Audible authorization information (I peaked in the file and it contained a single ‘data’ property whose value was 4 KB of encrypted something or other). Interestingly, even though I’d at this point authorized my Audible account in iTunes many times this week, the file’s date stamp was from last year, indicating the file wasn’t getting updated and thus my authorization went *poof* whenever I closed the iTunes application and its process died.
The Audible customer support rep first suggested to check the file’s permissions to make sure that my user account was authorized to modify the file. No problems there – I had read/write access to the file. Her second suggestion was simply to close iTunes, delete the Audible property file, open iTunes and reauthorize the computer. I did this and sure enough when I reauthorized the computer, a new property file was created with the current time as the timestamp and I was able to close and re-open iTunes without having to re-authorize.
Lessons Reiterated
This experience reinforces two software principles I already believed.
- DRM sucks ass
- Data persistence is hard
Solution Proposal
I sent the following suggestion to the Audible.com support person:
Thank you <redacted>. It’s working now.
FYI, it was not a permissions issue – the permissions were correct. I had to delete the com.audible.data.plist file and restart iTunes / reauthorize Audible to create a new version of the file.
I suspect this is related to my restore from Time Machine on to a new computer. I would suggest your engineers who work on the Mac iTunes integration test this case:
1. On a Mac, authorize to read Audible content via iTunes
2. Backup a Mac onto Time Machine
3. Restore from Time Machine onto a new Mac
4. Attempt to play Audible content
I’m not sure what the ideal behavior is (e.g. just working or requiring a single authorization of the new machine) but I know what should not happen is what happened to me 🙂
Thanks again for your help.
– Bill
thankyou this solves a big problem for me becase i cant always get intrenet access to reautherise the account
Wow! Same thing happened to me, after getting a new MBPro and using Time Machine to copy everything like it was on my old iMac (so I thought). I finally realized it must have been from that because nothing else had changed on my system. Interesting…
Of course, the Audible people hit a wall and were like, “Hmmm…well call Apple.” I ended up just unintalling iTunes app and helper and a few prefs, and re-downloading and installing. That did the trick. No more reauthorizing and having 17 hours of books disappearing off my iPods. The other annoying thing about that was that in the middle of a very long book, you have to find where you were in the book because iTunes resets the counter at the first chapter!
Anyway, thanks for posting this. It’s nice to know I wasn’t crazy. That audible preference file doesn’t show up though. Don’t understand why, but it’s not in there. Strange. Oh well, I’m not complaining.
Thanks again,
Greg
Oops. Add to that. The pref file IS there, but under the main hard drive preferences and not under my Home folder prefs.
Thanks for this, this very issue has been making me crazy, almost canceled Audible over it.
Thank you so much for the info. It helped me solve my iTunes~Audible authorisation problem. Cheers!
A google search led me to this post which ended up solving my issue which had been plaguing me ever since I restored a Time Machine backup to my new Mac Pro. I really dislike DRM. Thanks. (BTW the font size in your comment input form is almost impossible to read it’s so small:)
I don’t actually dislike DRM (usually) but I hate it when something goes haywire with the ‘blessing’ process and deprives me of rights that I originally acquired properly under the grantor’s terms and conditions. I had the same experience of authorization not persisting across iTunes launches after I used Time Machine to migrate my stuff from a macbook running leopard to a macbook pro running Snow Leopard. Thanks for your post, it worked like a charm to delete the existing plist and then redo the authorization.
Hey this looks like a great solution to my incredibly annoying issue. However I have no idea what it all means. Can someone help me in non-computer speak? Thanks
Derrick
I have a related problem. I bought (mostly for free) ebooks that I downloaded into my iPhone. I synced them into iTunes on my MacbookPro. Now they are in the laptop but have disappeared from the iPhone (since a software upgrade.) Why? And how can I get them back? Thanks for any help.
Leigh: I would suggest the following:
1. Connect your iPhone to your Mac via the cable
2. In iTunes, click on the iPhone icon on the left-nav
3. In the main area in iTunes, click on the “Books” tab
4. Ensure that your settings are configured to sync books (I just sync all ebooks)
thanks for hosting this info. interesting note now in 2014. I am being nagged for an Audible account password in itunes, but I have never had an audible account. the content is free content that has been on itunes for years. (Krista Tippet’s On Being).. no clue as to why I suddenly need an audible account to download free content from iTunes store but it is frustrating.. thought I would vent here. maybe someone else will stumble across this blog and have a solution.