Andrew McAfee has found a hole in the iTunes Store privacy model: if you try to gift music (or an App, or a Tv programme or film) to an iTunes Store user, iTunes warns you if the user already has that item.

This snooping process is iterative and cumbersome, but I'm pretty sure it could be at least somewhat automated. It's also a little fluky; to learn what I have, [the snooper] has to gift media to me in the same form I bought it. For example, if he sent me only a single episode of "Breaking Bad" season 3 iTunes wouldn't send him a message like the one above. This is because I bought the whole season at once, so [the snooper] has to gift me the whole season to learn about my purchase. Similar rules appear to hold for music.

Even though [the snooper] has to work a bit, I'm not thrilled that he (or anyone else) can so easily learn about my media purchases and tastes. If I want to share my iTunes holdings with my friends or broadcast them to the world Apple gives me tools to do so, but if I want to keep them private I can't.

McAfee says that Amazon handles this sort of problem differently; it simply converts duplicate items to store credit, informing the recipient of the duplicate items but not the gift-giver, and suggests that Apple would do well to adopt this approach. My online gift-giving is usually selected from users' wishlists so I've never encountered this problem in the wild, but if I were giving a gift I think I'd prefer to be given the chance to choose a different item rather than have my gift silently converted to an impersonal store credit: if I'd wanted to give an iTunes Store credit I'd have chosen that option. However, I can see that both approaches have their merits.¹

My feeling about this is that whilst it's technically a privacy breach, it's not a terribly scary one. The would-be snooper needs to:

1. Guess the email address I use with my iTunes Store account.²
2. Guess what music/apps/ebooks etc I might own and whether I bought them as individual items or as part of an album/season purchase.³
3. Automate this process so that Apple won't notice that some rabid fan of mine has made X attempts to gift me Y different tracks/apps/ebooks without ever going through with a purchase and throttle or block their access.

Having successfully negotiated those hurdles, the snoop is now in possession of … a listing of a small portion of the contents of my iTunes Library. Given that I display ample evidence of my taste in music on the internet for the whole world to see as a matter of course, you'll understand if I'm not terribly worried by this potential attack vector.

That being said, I do take the point that users who wish to keep their music choices to themselves should have the ability to do just that: Apple should probably get right on it.⁴

[Via Risks Digest]

1. Perhaps iTunes Store users should be allowed to specify in their account settings whether gift-givers should be warned of duplicates. ↩
2. Admittedly not everyone sets up a distinct email address to use just for iTunes, so this could be straightforward in some cases where the snooper already has your email address. ↩
3. Which raises another question: what if I have a track that I ripped from a CD in MP3 format and the potential snooper tries to gift me the iTunes Store version of that track in AAC/m4a format. Does iTunes recognise that it's the same track despite the format difference? ↩
4. Interestingly, McAfee points out that in the US it an offence to give out details of an individual's video rental/purchase history and suggests that if the iTunes Store makes it possible to find out what films a user has purchased this might leave the firm open to legal action. That sounds more like the sort of motivation Apple will need to close this hole. ↩

One of the features I've longed to see in iTunes is a way to tell it to play to the end of the current track and then stop. I've lost count of the number of times I've been enjoying a playlist and told myself that I'll just get to the end of this track then I'll go and [insert necessary but tedious task here] only to be swept along by the next track, then the next, then the next and found myself running half an hour late.

I'd seen a couple of Applescripts that tried to resolve this problem by checking the time remaining on the current track at the time they were called, waiting the appropriate number of seconds, then sending a Stop Playing command to iTunes. The problem is that there can be a significant delay between the Applescript starting up and it receiving the requested figure back from iTunes, causing the Applescript to play the first few seconds of the next track then stop abruptly. Not the end of the world, but not terribly satisfactory either.

Tonight I came across an alternative approach that looks to be 90% of the way towards being the solution I've been looking for. Tedw's Finish current track in iTunes playlist and pause Applescript works by disabling all tracks in the current playlist when the script is launched. This causes iTunes to stop playing when it reaches the end of the current track, as it finds that there are no more enabled tracks in the playlist. The script then idles for a few seconds before enabling all the tracks again. It worked beautifully, at least once I'd realised that it has to be saved as a Stay Open application so that it'll hang around long enough after being activated to enable the deselected tracks before quitting cleanly.

There is, however, one small hitch. If you're not playing from a playlist – e.g. if you've browsed your way to a particular artist or album and are playing it direct from the Library – then the script hangs and the album plays on. Having glanced at the source code, I think the problem is that the script is looking for a current playlist to work on and spinning its wheels when it discovers that there is no current playlist. Either that, or the method it uses to disable tracks doesn't work properly when applied to a non-playlist source. Either way, I ended up having to Force Quit the script. Not good.

That last 10% of functionalist is always the killer…¹

1. I don't have time tonight, but this weekend I'll have to take a look at the source code and read up in the iTunes Applescript dictionary and see if the script can't be modified to work around this issue. I'd have thought that it should be possible for the script to test whether it is being applied to a playlist or a Library entry – or iTunes DJ, or a Genius Mix, or another non-playlist source – and then, if required, send a Growl notification signalling the fact that there's no current playlist before exiting cleanly. Better still, I'd like the script to test for the type of object that contains the track currently being played first, then apply the playlist method when appropriate, or a similar method – if I can devise one – to non-playlist sources. ↩

Apple's iTunes 10.0.1 update makes an unwelcome change to the user interface:

iTunes 10.0.1 introduces a new feature: most items now have a 'Ping' dropdown button where the Music Store arrow links used to be. These appear even if you've disabled Ping.

The buttons cannot be disabled in the UI, but there's a Terminal fix to do it. [...]

There's also a huge Ping sidebar that pops up at the right edge of the iTunes window when you first open the updated iTunes, but Apple do at least provide an easy way to hide it by using a button at the bottom-right edge of the window.

I have a horrible feeling that every time Apple updates iTunes from this point on I'm going to have to to play whack-a-mole with that damned sidebar…

NB: the fix I link to above is for users of iTunes for Mac OS X only. Users of iTunes for Windows can find what look to be the equivalent instructions here.¹

1. As I don't use Windows I can't vouch for the efficacy of the latter fix. ↩

The terms & conditions for using iTunes include a boilerplate clause¹ barring persons in embargoed countries, or who are on various US government lists, from downloading and installing iTunes, or using that software for "any purposes prohibited by United States law." Or, to put it another way:

[All] the Al-Qaeda operatives holed up in the Northwest Frontier Provinces of Pakistan, dodging drone attacks while listening to Britney Spears songs downloaded with iTunes are in violation of the terms and conditions, even if they paid for the music!

[Via Bruce Schneier]

1. Prompted, most likely, by the fact that iTunes uses encryption to protect some of the content it downloads. Since the 1970s, encryption software has been in the same class as munitions – i.e. something that shouldn't be exported to hostile powers. ↩

What song does your iPod play when Shuffle-Fail strikes?

Mine is Take On Me by a-ha, because I have Album by Artist as my default sort mode. If I were sorting by song name it'd be Vampire Weekend's A-Punk.

Further to the previous post, it looks as if having your PDA confiscated could become a commonplace occurrence if the RIAA get their way:

A TOP-SECRET DEAL being ironed out by G8 nations will give the Music and film industry a state-paid force of copyright cops with the same powers of customs officials.

The copyright police can seize your mp3 player or laptop to see if it contains pirated content and can order ISPs to turn over personal data without the need for proof.

G8 members, at the request of those wonderful examples of humanity at the RIAA, are agreeing to turn tax-payer paid customs officers into boot boys for the record and music business.

The Anti-Counterfeiting Trade Agreement (ACTA), will be discussed at the next G8 meeting in Tokyo, in July. [...]

Just one small, practical question: if I hand my iPod over to a customs officer, how exactly will he or she be able to tell which tracks I downloaded from iTunes and which ones I ripped from my CD collection? On my (fairly old) iPod, there's no way to tell at a glance, since the software doesn't visibly distinguish between AACs and MP3s.¹ There is a 'Purchased' playlist, but that only shows files purchased on my current Mac; it doesn't pick up purchases made on my previous Mac and transferred over to this one. Will I be OK as long as I refrain from setting up a playlist called 'Illegal copies', or do I have to start carrying copies of my invoice emails from iTunes around with me if I want to leave the country?

[Via Memex 1.1]

1. Not to mention that some iTunes purchases will be MP3 files, and some MP3 files will come from other stores like Amie Street or eMusic. ↩

I Love Stars does one thing and does it well: it sits in your menu bar and pops up the star rating of the song currently playing in iTunes, and allows you to amend the rating by clicking on the appropriate number of stars.

Neat, compact, unobtrusive and free. What's not to like?

(NB: I Love Stars requires Mac OS X 10.5, aka Leopard, to run.)

[Via dsandler]