I’ve had a rather torturous affair with iTunes 11 thus far. While there are some general improvements for non-power users such as album view and dragging to playlists, these have (unnecessarily) come at the cost of making life very, very difficult for power users, if not otherwise tedious and inconsistent for all.

Let’s take a look at some key features of using your music library to see where Apple’s gone off the rails with this update.

Things people do on the regular, like importing CDs (although this must be a passé ritual since new Macs no longer shop with optical drives); managing your iTunes library and file storage; viewing and finding your music. By no means a definitive list, but an embarrassingly long one, nonetheless.


Here are four wonderful iTunes 11 design decisions which slow down the importing process:

1. Previously when importing, you could just pop the CD in and set it to auto-import. No more. You have to click the Import button. Every time.

2. This would perhaps not be so bad if you could just hit the Import button, but not even this is a one-step process. With iTunes 11, a dialog comes up to confirm the import settings. Who changes import settings with every import? This is a completely unnecessary extra window and click in the now doubly tedious import process.

3. If you are comparing an existing import to a CD (for example, I’m currently trying to upgrade a bunch of 2003 iTunes 128k imports to 320k imports) you used to be able to go the album, take a look at the bit rate, compare track names, edit the CD track names, import, and jump back to your library to double-check all the songs were replaced and no duplicates imported.

Now, the default view for iTunes is album view which doesn’t show you the bit rate or genre, so you have to switch to another view (Songs, Playlists, etc) to confirm bit rate and genre (along with track name, artist, year, and album name), then change to the CD view, update the details there to match, and import.

This is a multi-step process because there is no way to see both the CD view and existing album view at the same time. And to make this an even more tedious process, when you switch back to the music library from the CD view, you are greeted with a default Album view. In other words, not only are you not in the view you were last in, but even in Album view, the album you were last looking at is not selected, so you have to search for the album you’re importing once again. So, so tedious.

4. Making this even more of a nightmare to manage, it appears that with iTunes 11, even when files are reconciled in iTunes and the 128k file now shows as 320k in your music library, both the 128k and 320k file are saved to your hard drive. So now you have a duplicate of every file on your computer, though you’d never know if you didn’t look at your hard drive.

In every previous version of iTunes, reimporting would delete the older file, keeping only the new one.

Now, you could argue this isn’t that big of a deal. Why not just delete the crappy 128k version and import the new CD all over as 320k. The trouble here is, this gets rid of play counts, ratings, and removes the songs from any playlists they were ever manually added to. For someone who has smart playlists set up and is fanatical about putting songs into playlists to keep them organized, this is even more of a nightmare than dealing with duplicate 128k files on a hard drive.

In any case, you’re left with the following import options with iTunes 11:

  1. Destroy all your smart playlists by deleting lower bit rate imports and reimporting your CDs at your desired higher bit rate.
  2. Import your CDs overwriting previous imports and use Finder to delete all the duplicate lower bitrate files manually.
  3. Suck it up and keep listening to poor quality files from 2003.

Managing Files

This past week’s update to iTunes 11.0.1 brings the duplicate files view back. Alas, this ‘feature’ continues to be useless. More on that and a couple of other tedious file management issues.

1. iTunes still makes no effort to discern the difference between the same song on a different album vs the same song on the same album with the same or slightly different criteria. (ie, a true duplicate and/or a file with a different duration or bit rate that’s off the same album, and so on. For that, you’ll need to ask Doug for some help.

2. Missing files are still referenced only within the play order column, so there’s no way to sort your library by missing files and deal with them directly. And I swear around iTunes 10.4 or so you could select one missing file and match it and iTunes would attempt to match all the other missing files based on the same file structure. But, that certainly has not been the case for many years, so you’re left dealing with missing files one at a time. If you can even find them.

3. Renaming an artist, genre, album, or otherwise, causes any search or list to be reset to  once that item disappears from the list. I suspect this is an issue with everything being stored in a single XML file, but that just points to the fact that iTunes 11 uses the same sorry guts of every previous iTunes. ie, it’s 10 years old and is sorely in need of being rewritten to improve performance, if nothing else.

In fact, renaming a song in a list jumps that song to the top of your list (even if you’re sorted by album. This new and unnecessary behaviour is confusing. Your list shouldn’t be jumping around at all. Ever.


Then there are new limited view options which make navigating your library more cumbersome than ever.

1. Multiple windows, for one, are gone. If I could open the CD I’m importing in a separate window, I could avoid the reset of the Music library view (described above) when I’m comparing an import to a CD.

2. And while making playlists by dragging to the right has it’s benefits when you’re just noodling around, there are three major issues with this interaction:

i. it only works in certain views. If you’re in Playlist view or have the Sidebar open, for example, dragging left inexplicable does nothing.

ii. if you’re trying to create a Playlist from multiple locations in your library (ie, doing a lot of jumping around or searching to build a playlist for, say, a house party, or wedding, or to romance someone, it’s far, far easier to open this in a separate window and drag and drop, which leads to the final point about creating manual Playlists;

iii. with a separate Playlist window, you’re able to drag and drop in the order you want. ie, you can put a song between track 3 and 4. With the sidebar option, you’re just dumping a bunch of songs in a list and you have to go that Playlist later to order them. Again, this is unnecessarily tedious.

To be fair, iTunes does offer a new Edit Playlist view which anchors the playlist on the right hand side of iTunes and switches the main view to song view so you can move any song into the Playlist. But this hides all other Playlists, so if you want to drag from any one playlist to another, your only option is to turn on the sidebar and move one song at a time because, of course, if you show the sidebar, Edit Playlist no longer works, and vice versa.

Just another mindless inconsistency that makes getting used to these new, limiting features, a nightmare.

3. Back to general views, we now have a dropdown view selector with List, Artist, and Album view.

And within Artists view you get this hybrid list view with album art, but no standard album view.

Meanwhile, with all the effort to make the library more artwork friendly, there’s an odd-ommission: the removal of a Cover Flow view means any single artist track playlists (best ofs, compilations I’ve made, etc) now has no artwork. Previously, I’d flip on Cover Flow so as we moved from track to track the artwork for that song would show. Now there’s only plain old list view, or Artist view, which shows massive gaps between each individual song.

And we have the command B viewer

And, as a quick aside, what’s with the scrollbars in iTunes 11?

4. And now we have 4 different play/pause buttons and 4 different shuffle buttons (which seem to offer completely different and sometimes annoyingly unclear shuffle options. Here’s the rundown:

i. The Shuffle toggle in the header allows to turn on or off shuffling of the currently playing song, retaining whatever your last shuffle settings were.

ii. The Shuffle toggle in a Playlist shuffles the entire playlist, restarting the playlist with a random track, even if you were listening to a track in the playlist.

iii. The Shuffle toggle in a Playlist that sits beside an artist name shuffles all tracks by an Artist across your entire library, not just in the Playlist you were listening to.

iv. The Shuffle toggle beside an Album name shuffles only songs in the album. ie, if there’s one track in an album and you hit this Shuffle button, you hear one track and that’s it.

In other words, there doesn’t appear to be any way to shuffle a variety of songs from a currently playing track. Well, unless you hit the arrow when you hover over the track name and select ‘Start Genius’; that’ll shuffle the song in with others, of course. Well, if Genius has any suggestions for that song.

Finding Music

1. Speaking of that arrow that’s revealed when you hover over a track name. There’s all sorts of good stuff in there. Sometimes.

5. Default search searches across all of iTunes, not just Music. This is important if you’re using a large library as it will freeze iTunes for several minutes, if not for good. This is said to be improved with iTunes 11.0.1 but I thankfully found you can change the default search to avoid this cross-iTunes music/app/book search (who would ever need that?!)

Tagging Music

There are a few improvements, quick access to making folders, for instance.

Rating is two steps in the mini player, and oddly, they’ve removed the stars from the doc rating view and replaced this with numbers 1 through 5.

The ‘cut’ command no longer works if you try to cut the last name of multi-name artist. That has to be a bug.


In fact, this update is so clearly a disaster that there’s a disconnect between the actual shipping product and the marketing screens on Apple’s website.

Every view of songs in the iTunes library on the iTunes Player section of the Apple site shows the sidebar open even though it’s closed by default. No doubt this is because it’s just about  the only way to find Genius Playlists. The caveat being that if you select the Playlists view you can now see Genius Mixes and your latest genius mix at the top of the Playlists column. But this was clearly a last ditch effort to get Genius Mixes back into the new design as the What’s New in iTunes video does not show these at all. I can just see the meeting now where someone said, “Where can I find Genius Playlists?” And after a few futile clicks they delay the release a month.

And all of this without rearchitecting the app at all so it doesn’t rely on an extremely slow flat file database. At least if there were some performance improvements, we could enjoy those while we wait for the nightmarishly cumbersome and inconsistent design issues to  be addressed with subsequent updates.

Alas, all I’m left hoping for now is that they quickly address the inconsistencies in behaviour across different views and the file management issues before I run out of patience and attempt a downgrade to 10.7. In the meantime, I’ll try to focus my time on enjoying the Mini Player and trying to find some excuse to use the album view as those are, as far as your music is concerned, about the only discernible improvements over iTunes 10.7.