How I Would Fix iTunes, Part 6: Fix Syncing

(This is one of a series of articles looking at elements of iTunes that I think need fixing. I’ll choose one element for each article, and offer a solution. See all articles in this series. If you have any particular gripes about what needs to be fixed in iTunes, drop me a line.)

iTunes syncing is a disaster. I’ve written about it several times on this website, and in my articles for Macworld. Following this article – which is the most popular article on my site, every day – dozens of iTunes users have commented about their experiences. And a Macworld article I wrote about this problem has nearly 100 comments.

The frustration level of users unable to sync their iOS devices with iTunes is quite high, in part because they find little or no help from Apple support or Genius Bar. I’m repeatedly told that users who contact Apple hear that the support teams aren’t aware that this is a problem, and users can spend hours doing what Apple recommends – essentially, restoring their device and re-syncing everything – only to find that the problem re-occurs almost immediately.

To be fair, millions of iOS users have no problem syncing. In fact, I’d wager that most iOS users never sync their devices. They download apps, perhaps some music, but keep it all on their devices (which also means they have no backups). But the sync problems seem to arise once users have a substantial media library. iTunes can certainly handle large libraries, but iOS devices seem to be unable to accept them.

While these problems have existed for many years, it seems that they’ve reached critical mass with the introduction of iOS 8. When I briefly had an iPhone 6, I found that, after the first sync, it was nearly impossible to add any new content to it. I get emails almost daily from people experiencing the same issues, with all types of iOS devices, but the iPhone 6 does seem to be more prone to sync problems.

So, two things need to be done. First, Apple has to recognize that this is a problem, and not have their support teams act as though it’s something new and rare. Apple has a history of pretending that nothing is wrong, until they admit that there was a problem. Remember antennagate (“You’re holding it wrong.”), or the video problem with 2011 – 2013 MacBooks Pro, that the company only recently announced that they would fix? They constantly pretend that there’s user error, rather than deal with the issues, because an admission of a problem in their hardware or software would potentially lead them to an expensive recall or replacement program.

Second, Apple needs to fix syncing, period. If you buy an iOS device, you expect to be able to sync your content. If not, the device is simply not fit for purpose. There’s no excuse for selling a device which Apple claims can do all these wonderful things, whereas something as simple as copying music is fraught with so many problems.

It’s clear that none of Apple’s senior executive sync their iOS devices with iTunes. They probably have everything they want in the cloud, and never experience the type of problems that rank-and-file users encounter. I expect that if Tim Cook, Eddy Cue or Jony Ive had this kind of problem with their iPhone, it would get fixed pretty quickly.

How I Would Fix iTunes, Part 5: Make it Possible to Turn Off Up Next

(This is one of a series of articles looking at elements of iTunes that I think need fixing. I’ll choose one element for each article, and offer a solution. See all articles in this series. If you have any particular gripes about what needs to be fixed in iTunes, drop me a line.)

In iTunes, whenever you play any music — unless you are playing a playlist which contains just one song — there is a song queue. It may be all the songs of an album, all the songs of a playlist, or all the tracks in your library. You can see the song queue at any time by clicking the Up Next? icon in the iTunes LCD or MiniPlayer.


The Up Next icon is the one with the three lines at the right of the Mini Player window above, and there’s a similar icon in the iTunes LCD, the part of the iTunes window that shows you what is playing.

The problem is that you may have music in the Up Next queue without realizing it, and when you go to play something else, you may see what I call “the pesky Up Next dialog.”

Up next dialog

This dialog displays when you have explicitly added music to the Up Next queue (the Up Next icon in the iTunes LCD is blue), and you then try to play something else without first adding it to Up Next. For example, you might have double-clicked an album or playlist. (The dialog is slightly different if you double-click a single track.)

If you click Clear Songs, iTunes replaces your Up Next queue with the tracks in the item you just double-clicked. Or, if you click Don’t Clear, iTunes adds what you just double-clicked to the beginning of the Up Next queue; this is the same as if you had Control-clicked the item and chosen Play Next. Of course, you can click Cancel to keep listening to what’s currently playing.

Up Next also gets in the way when you select an album to play using the Remote app in iOS. Sometimes I’m listening to music in my bedroom, where I have an AirPlay speaker. I choose an album to listen to, and, when it’s finished, I hear the next album in my iTunes library. The Remote app doesn’t show that album in the queue, yet, once the album has finished, it starts playing, and the queue is full of everything from that album to the end of my library.

Confused? So am I. I’ve gotten lots of queries about Up Next, and it’s very hard to explain; it’s even hard for me to understand what exactly is supposed to happen.

Up Next is confusing, especially because users will find that it gets in their way when they do something as simple as wanting to play some music. Apple could fix this by allowing users to turn off Up Next if they want. This is a simple change that would make playing music in iTunes a lot less confusing.

How I Would fix iTunes, Part 4: Increase the iTunes Match Track Limit

(This is one of a series of articles looking at elements of iTunes that I think need fixing. I’ll choose one element for each article, and offer a solution. See all articles in this series. If you have any particular gripes about what needs to be fixed in iTunes, drop me a line.)

When iTunes Match was first released in November, 2011, people already judged Apple’s 25,000 track limit (for match tracks; purchased tracks are unlimited) to be stingy. Sure, not everyone has a large music library, but the 1% of iTunes users who do are the prime demographic for this service, and they were immediately judged nebula non grata.

Itunes match limit

More than three years later, that limit is becoming a problem for many music lovers. If you have a lot of CDs, or buy a lot of music, it’s pretty easy to hit that limit, as you rip and match more of your CD collection. It’s especially problematic for those with large classical libraries; many classical box sets contain 50 or more CDs, swelling the size of a music library very quickly.

Apple needs to increase this limit, if only to keep up with the competition. Google Play Music has just increased their limits from 20,000 to 50,000 tracks, and it’s free. Amazon’s Cloud Player lets you store 250,000 tracks, for the same price ($25) as iTunes Match.

Arguably, these are different types of services. iTunes Match matches your music, so you don’t have to upload it all; if I had to upload my music library, it would take years. And iTunes Match updates quickly from iTunes, whenever you add or delete music. Amazon and Google are merely music lockers, where you upload all your music, and play it when you want.

Apple clearly needs to increase the iTunes Match limit. Unless they’re planning on dropping the service, they need to follow the needs of users, and more and more people have been emailing me recently asking how they can deal with an iTunes Match library that is approaching the limit. (It’s not always simple to deal with.) Perhaps Apple can charge more for a higher limit; or perhaps they can just increase the current limit. Or maybe they could finally allow users to choose which of their tracks get uploaded to iTunes Match. But 25,000 tracks, which may be a lot for the majority of users, isn’t enough for serious music fans.

How I Would fix iTunes, Part 3: Multiple Windows

(This is one of a series of articles looking at elements of iTunes that I think need fixing. I’ll choose one element for each article, and offer a solution. See all articles in this series. If you have any particular gripes about what needs to be fixed in iTunes, drop me a line.)

Until iTunes 11 was released in 2012, the app let you open multiple windows. You could have, say, one window showing your Music library, and another displaying the iTunes Store. Or you could open two windows when you were creating playlists: one you’d use to browse your music, and another with your new playlist, allowing you to drag and drop items from one to the other, and re-order them easily.

While most iTunes users didn’t use multiple windows – and probably didn’t know they existed – many of us miss this feature. It is most obvious when I visit the iTunes Store. If I’m in my Music library, I need to click the iTunes Store button, then click the type of content I want to browse. If I’m in the iTunes Store and want to get back to my library, it’s often two clicks to do this.

I know why Apple did this, at least in iTunes 12: every time you leave the iTunes Store, clicking a media kind (in the navigation bar at the top left) takes you to another section of the iTunes Store. So, before you leave the store, you may see more things to buy.

Unfortunately, this just makes using the iTunes Store more annoying. I used to always have a window open for the iTunes Store. I could check music, movies, or apps, and not lose my place in my Music library. I could quickly get back to exactly where I was in one of me media libraries, instead of having to click several times to get back to the same library, and the same content I was looking at before.

It’s not complicated to bring back multiple windows in iTunes; they could even do it with tabs, as in Safari and other web browsers. It’s one of the main features I’d like to see fixed.

How I Would fix iTunes, Part 2: Better Tagging

(This is one of a series of articles looking at elements of iTunes that I think need fixing. I’ll choose one element for each article, and offer a solution. See all articles in this series. If you have any particular gripes about what needs to be fixed in iTunes, drop me a line.)

iTunes – at least the part that manages media files – is simply a database. It reads information embedded in media files, and then presents that information in its windows. This information – also called metadata, or tags – can be text or graphics; the name of a track, the artist’s name, or album artwork. iTunes reads the ID3 tags in files and displays them.

Tagging files is therefore the key to their organization. They allow you to browse files by genre, artist, composer or album. They let you search for items in your library. And they enable smart playlists, which find files that match certain conditions. (And, of course, without tags, you also wouldn’t be able to search the iTunes Store.)

While ID3 tags are widely used, there is no actual standard for them. Some apps add their own tags to files, which other apps may or may not be able to read. This means that, other than for the main, well-defined tags, anyone is free to write what they want in files. You could write a music management app that has all sorts of extended tags (in fact, I know of one person who has).

One gripe about iTunes is that tagging is limited; notably in the genre field. With music as amorphous as it is, pigeon-holing a song or track to one specific genre is not always possible. As I write this, I’m listening to a set of recordings by Pierre Boulez of his own compositions. There are a dozen CDs in this set, and, when ripping them, I have to decide how to classify them. I don’t use the “Classical” genre for my music; that is meaningless. Instead, I use custom genres, such as Keyboard, Chamber Music, Orchestral, Vocal Music, and more. But, with classical music, it can also be useful to have a genre that represents a time period. For example, I could have Early Music, Baroque, Romantic, 20th Century, Contemporary, and Avant Garde.

The problem with any such genres is that one is not enough. Does it make sense that Keyboard includes, say, Bach’s Goldberg Variations played on harpsichord and Charles Ives’ Concord Sonata played on piano? Is it logical that Orchestral include Haendel’s Concerti Grossi and a Mahler symphony?

One workaround for this is two use two-word genres. For example, you could have Baroque – Keyboard, and Orchestral – 20th Century. I find that unwieldy, because it creates far too many genres if you really want to label your music.

What iTunes needs is tokens in the Genre tag, as well as some other tags. Here’s how this would work. You would be able to enter multiple items in a tag field, and separate them with a comma. When you press Return, iTunes would parse them and create individual tokens, like this:

Multiple genres

In this manner, you could tag Bob Dylan’s music as Folk, Country, Rock, or Gospel, according to each song or album, with a master genre of, say, Dylan. You could organize music by decade, with Rock and 90s both listed for your Nirvana albums, Be Bop, Jazz and 40s for your Charlie Parker recordings, and Pop and 60s for your Beatles albums. When you browse your iTunes library, you would find that Pink Floyd’s Dark Side of the Moon might show up in several genres, such as Rock, Progressive Rock, and 70s, according to the tags you’ve added. And why not create mood genres as well: Workout, Chillout, Instrumental and other genres are all possible.

But it shouldn’t stop here: these tokens need to be available for the Artist tag as well. For Leonard Bernstein’s recordings, of which I have many, I don’t want to create a separate artist for Leonard Bernstein together with each orchestra he recorded with; I want one Artist entry for Leonard Bernstein himself, and another for each orchestra. I’d like to be able to easily find all my recordings of the New York Philharmonic, regardless of which conductor led them (in fact, this is an interesting way to explore the recordings of an orchestra). For jazz, I’d like to be able to find, quickly, all recordings I have by John Coltrane, both as leader and as sideman (such as his recordings with Miles Davis, Theolonius Monk, and others).

One problem with these tags is that they may not be portable; transferring the files to another app may lose some or all of the tags, or may group them together in a single tag. So what? If you’re using iTunes in this way, you’re unlikely to be switching to another music player. As long as the tags don’t get deleted, I think it’s fair to allow iTunes to use its own system.

This is really a feature for power users, but I’m sure Apple could spin it for others as well. Look at the popular charts and see how many songs include “featured” artists; as I write this, four of the top ten songs in the iTunes store include featured artists, which are listed like this:

Featured artists

Apple could sell the idea of multiple tags even to listeners of popular music as a way of finding their favorite artists when they are not the main artist on an album.

Multiple genres are needed; tokenization of tags would be a boon to anyone who tags their music. If iTunes could add this feature, its music management would become much better and more flexible for all music lovers.

How I Would Fix iTunes, Part 1: The Info Window

(This is one of a series of articles looking at elements of iTunes that I think need fixing. I’ll choose one element for each article, and offer a solution. See all articles in this series. If you have any particular gripes about what needs to be fixed in iTunes, drop me a line.)

Update: Apple has fixed the Info window, in an update released on April 9, 2014.

iTunes 12 changed the Info window, the window that displays when you select one or more tracks and press Command-I. You use this window to tag files; to edit the metadata, such as the track name, artist, album name, and more. But this window is poorly designed, for several reasons.

First, take a minute to think about how you tag files in iTunes. For most users, the tags you want to edit are the Name (song or track name), Artist, Album, Genre, and perhaps a couple of others. In the previous iTunes Info window, these tags were all grouped in the same area at the top of the window.

Info single

But the new Info window separates these tags. The Name field has become Song Name, which is perhaps clearer. The Artist field comes next. But then comes Composer, which you mostly use if you’re tagging jazz or classical music. The Album tag is near the bottom of the window, followed by Album Artist.

Itunes new info single

This means that, for most users, tagging will no longer involve typing and pressing the Tab key a few times, but looking closely at the window to find where the fields are, and manually clicking in different locations.

Why would Apple decide to put the Album tag near the bottom of the window? This is one of the most important tags for music. And why would they promote the Composer, and even the BPM tags? This design was clearly made by people who don’t tag music in iTunes.

In addition, they’ve stacked some of the shorter tags vertically, using up a lot of space, rather than, say, putting two per line.

Here’s a mock-up of what would be a much better layout for this window.

Info window copy

It not only puts the tags in a more logical order, but it is more economic. It’s perhaps a bit dense, but it’s a lot more useful.

Since the Info window is an essential part of iTunes, at least for those people who either rip CDs, or change tags for music that they’ve purchased or downloaded, it needs to be user-friendly and logically designed. That’s not the case with the current version of iTunes.