The Trouble with iTunes on the Mac and Windows

For a company that prides itself on providing a top-notch user experience, Apple ought to hang its head in shame for the disaster that iTunes has turned into. It's a bloated, piggish, unreliable mess. It's the application we love to hate. It's the application that some of us just hate. But we put up with it. Because we have no choice.

A Brief history of iTunes

iTunes started life simply enough - it was a tool that we used to listen to music. "Rip. Mix. Burn." That was Apple's simple message - rip the music you already owned on CD into digital music files. Create your own playlists. And burn CDs containing your music so you could listen to them elsewhere.

Rip. Mix. Burn.

Then the iPod came along and everything changed. Suddenly we no longer used iTunes just to rip and mix our music, but also to move it to this device that fit in our pockets and stored a thousand albums. iTunes was fun to use, too - you could sort music by genre, rate the songs you liked, and drill down with terrific levels of detail, assuming it was available in the metadata - stuff like composer, release date and more.

The iPod grew and so did our music collections. Many of us began to look for other ways to get music, through file sharing services and other means. So Apple's next step, the iTunes Store, made a lot of sense. It made it easier to get music online, and it provided musicians and their labels with a revenue stream.

But the iTunes Store introducing another layer of complexity into iTunes - now we weren't just using iTunes to store and catalog our music, but to buy it as well. And that meant incorporating copy protection into the mix - Digital Rights Management, or DRM.

When Apple introduced iPods to be able to run applications and watch video, the iTunes Store - and the iTunes app - again increased in complexity. You could do so much more with iTunes than you could before. You could grab movies and TV shows. Copy protected using the same DRM scheme as music - Apple called it FairPlay. Eventually FairPlay copy protection disappeared for music, but it's lingered for movies and TV shows.

Then the iPhone came along, and eventually the iPod touch and the iPad followed. And suddenly the iTunes Store grew more in complexity - now it was selling apps through an App Store. Apple decided to take on Amazon and the Kindle by offering ebooks, which added another layer onto iTunes. And so on, and so on.

iTunes Match

The latest addition is iTunes Match, Apple's $25/year service that makes your iTunes music library available in the cloud, downloadable to any device authorized to play it. And when iOS 7 debuts this fall you'll be able to listen to iTunes Radio, streaming content that is ad-free if you're an iTunes Match subscriber.

iTunes has become a shambling monstrosity

One can't fault Apple for continually trying to add more features to iTunes. But iTunes has become a wall with many layers of wallpaper stuck to it, each glued and layered on top of the last. Eventually they have to come off, and what you're left with is a wall that needs to be refinished before it can be repainted.

The net result is that iTunes does a lot of things, but does them poorly. The interface has become needlessly complex, and attempts to refine and improve it have largely failed as a result. iTunes is the one Mac app that drives your experience with music, downloading television shows, movies and apps. It's trying to do too much. It needs to do much less. As a result, even the name "iTunes" has lost its meaning - "tunes" are only a small part of the app's overall function.

For my part, I have a seemly endless variety of problems with iTunes. With over 23,000 files, iTunes crashes for me frequently and is terribly slow. I lost last weekend trying to download my iTunes library from iTunes Match, after the machine that held my original library went out for repair. The entire weekend. Because iTunes kept crashing and stopping the download.

iTunes quit unexpectedly - quelle surprise

iTunes Match enables me to download music when I'm on my phone when I'm out, but often forgets about album art. iTunes Match on the Mac is far from perfect, too - it has, for no good reason, keeping me from downloading dozens of tracks that I've uploaded. They're grayed out, and Apple hasn't been able to fix it for me (and logging out and logging back in hasn't helped).

Music I can't download

iTunes' duplicate finding capability is miserable. And it often can't find the cover art I'm looking for, or substitutes something else entirely in its place. It's little wonder that utilities like TuneUp exist - they have to, because Apple's done such a poor job with iTunes, some users need help sorting their iTunes libraries.

Time to break up the party

"True simplicity is derived from so much more than just the absence of clutter and ornamentation," explained Apple senior vice president of Design Jony Ive in the intro video for iOS 7. "It's about bringing order to complexity."

I think it's time for Apple to look at iTunes and start over with a fresh sheet of paper. Just admit that this horrible thing isn't working any more and try something entirely new. Ideally, I'd like to see music, apps, and videos broken up into separate utilities.

"Complexity" is a word that describes the iTunes experience to a tee. Hopefully once iOS 7 is out the door, Ive can put his eyes and his best minds to work on the problem of iTunes, because right now it's embarrassing for Apple to be promoting and distributing this software. It's the antithesis of what we expect the Apple user experience to be.

Do you hate iTunes as much as I do? Or do you love it? Do you accept it as a necesary evil? Or do you use other utilities entirely? Let me know in the comments.

104 Comments
  • Don't love it... don't hate it either. It has moments of total annoyance... it does what I need it to most of the time... :)
  • Ditto. I use to really hate it when I first used it back on Windows with the first iPod nano, but now it does it's job and I have no complaints.
  • I know I may be in the minority, but I actually have no problem with iTunes. I have a music library of 20,000+ songs, a dozen or so movies, a few TV shows and music videos, 100 or so iOS apps, and some ebooks. For me, iTunes is snappy and responsive, and very rarely crashes. The way I look at it, iTunes is the repository for all my media (aside from photos), and the interface for my iOS devices (iPhone and iPad), and I kind of enjoy being able to go to one place to access, manage, and distribute it all. That being said, I'd be curious about a revamped approach to iTunes, but the thought of multiple stand-alone apps taking the place of what iTunes now does isn't that appealing.
  • My sentiments exactly, I just don't get all the anti-iTunes arguments at all. I have 3800 songs, 163 apps, and subscribe to 10 podcasts. iTunes keeps them all updated and when I plug in my iPad, iPhone, or iPad Mini they are synced with no problem. I don't want to have to launch 4-5 different apps and sync each one individually, or manually, that's ridiculous. iTunes works just fine.
  • Consider the iOS model - there are different apps for ebooks, video and music. One place to buy them (except for iBooks) - iTunes - but different places to actually use them.
  • Right there with you. I used to do tech support and IT maint. for a major BPO company. That experience (not to mention 9 Xbox 360s with the ring of death) have made me despise anything associated with Microsoft in even the most remote way.
    While there is room for improvement, I find it the most simple and user-friendly system for its purposes. I for one am sick of needing to subdivide every single thing I do. Having a single central place with witch to store and use my media without an app or program running for each is preferable to me. I disagree with the less is more theory entirely. Why do we have smartphones? People were tired of having a device for calling people, another for navigation, another for checking emails and IMs (back in the day). Smartphones were born. I feel the author is clinging to the past too much. Admittedly, iTunes may not be the best name to describe what it does, but I'm sure you all know the reference to a 'rose by any other name'
    In further contradiction to the above mentioned opinion, I believe that Apple is growing with their apps/programs much the way the smartphone did. iOS 7 is proof of that with the integrations and built-in features it adds. If you follow these lines of evolution, you'll see that one day, iTunes (or whatever it is called by then) could be a central entertainment hub. Possibly partnering with others trying for similar ideas in various forms of entertainment, such as Steam, a similar system to centralize and reward video gaming. Even live, streaming television shows and news broadcasts. Along those lines, it could replace satellite/cable tv altogether eventually (or at least be a strong competitor). These are all "ifs" but nevertheless, would be impossible by slowing down and subdividing the system.
    If you want to make 'Apple Media Center' the name and split it into 'iTunes', 'iMovies/TV', 'iPhoto', and so on, then fine. But it's the same thing and we are only arguing semantics.
    If you want everything separate, try MS-DOS.
  • I'm in the same boat as you. Literally to the count. In my house, we use Apple TV's for all media consumption, with iPap's and iPhone's supporting them and syncing to iTunes. No crashes, no issues. But I really needs to be fixed. It's messy. The ability to detect duplicates and automatically delete them, find artwork, all spot on.
  • I agree ChicagoMatt!! I think its the trend to complain about iTunes. I RARELY if ever havea problem with iTunes. If you don't like try something else and see how that works for
  • Great piece, Peter. You sum it up in saying that iTunes is the antithesis of the elegant simplicity Apple strives for. I like Apple products for the most part, but I truly bemoan iTunes and their approach to mobile file management in general.
  • I think you have hit the nail on the head, iTunes needs to be split into separate apps. One for music/videos, one for Apps, and one for ebooks. The app management aspects of iTunes are so dysfunctional it is ridiculous. Great article! Hope somebody from Apple reads it.
  • Great article Peter! While iTunes works for me 95% of the time (its slow to start up and also gives me the wrong Album Art for a few albums causing clean versions of songs instead of explicit songs to be uploaded to iTunes Match) its nice for what it is. Like other have stated iTunes needs to broken up into separate apps for different stuff, and we may or may not see that happen in in iOS 7 but hopefully it will happen in future iterations of iOS.
  • On my 2012 13in" Macbook Air, iTunes runs ok. However, when I buy vinyl and get download codes, adding to the library crashes nearly every damn time. I have 30,000 songs. They screwed up the column browser in iTunes 11, which made me rage harder than ever. There is no good alternative for listening to locally stored music.
  • I have a feeling iTunes crashed right before you wrote this article. Seriously, though I have zero issues with the app aside from the fact that it needs to break itself into several streamlined apps, which I bet will happen with OS11. Have you used Spotify or Mog? There is no comparison.
  • I really can't say much about iTunes because I just don't use it. I ditched the iTunes model for buying music, and get all of my music off of Spotify. For Movies and TV Shows, well, I don't watch them through iTunes but use Netflix and Hulu. Obviously, I have to use iTunes for apps, but I don't purchase iPad/iPhone apps via my computer, but from my device. Now, I don't even have to connect to my computer to get the latest update, but can do it straight from my device. I can't even remember the last time I have opened iTunes on my Mac(and probably only because of accidentally pressing the icon in my dock). The alternatives to iTunes features, are much better in my opinion. One thing iTunes does excel at is content management, there is no one better, but since I have basically branched my content off to all the listed services, I have no use for management. I have nothing against iTunes, and when I did use it, I loved it, but I have moved on and am very happy for doing so.
    Great article Peter! :-)
  • This is less than useful. It's just a "boast post" or outright SPAM. "I'd like to reply to your article about cars, by talking about my bicycle." (roll eyes)
  • That is your opinion and you are more than welcome to it. I can assure you that my intent was not to boast or create a spam post. All I was trying to say, it that there are a lot of other services that I have found to replace iTunes, that are in my opinion better, so I can't really say much about how well I like iTunes. Maybe, I went into to much detail for your liking, and I am sorry if I caused you any emotional distress over it, but I was just trying to put the reader to a point where they could understand my position. Again, I have nothing against iTunes, and think it is a great service for managing content, as I said, there is "no one better".
    Thanks for the reply! :-)
  • Not going to lie, I can't stand iTunes, it is not user friendly and really has become a mess now. Since I use many different systems besides Mac, I have dabbled in many programs and the sad part is there is no one program that simply works. Out of all the music programs I have tried, the one that has worked best for me was Zune for Windows (imo), but now with that scrapped there is Xbox Music which is just as bad as iTunes (if not worse in many aspects). Now I just use a shamble of music programs: Pandora, Spotify, Slacker Radio, Zune, Xbox Music, and iTunes; but it would be really nice to simply use one cohesive program for my music collection and organization. I expect better of Apple and hope that they can get back to a theme of simple elegance with later versions of this program. I think they shouldn't have separate apps for TV & Movies, eBooks, etc... But I think something new and fresh could really help iTunes out.
  • I actually enjoy using iTunes and I think it has matured and improved as the years have gone by. I have over 30,000 music tracks, about 150 HQ movies, I use Match, and I have thousands of saved podcasts. I have never had a problem with iTunes crashing on any kind of a regular basis. I like the UI and the UX it provides. I like the fact that I can manage my iPhone, iPad, and iPod classic 160GB using just one application. My MIDI turntable DJ mixing software works flawlessly with my very well organized library (which I easily keep organized without using third-party tools) and playlists. Never a problem downloading content from the cloud, and Amazon's downloader for digital content works with my iTunes library without any issues. The only thing I have to complain about is the lack of variety for visualizations and a tool to create your own like what Winamp offers on my crappy Windows 7 work computer - but I rarely ever turn on visualizations so not that big of a deal. And, iTunes is beautiful to look at and very well integrated on my Mac computers. The one suggestion of yours that I really take exception with is the breaking apart of iTunes into multiple applications based on media type. Such a move would actually introduce more of the complexity you believe needs to be addressed. Are users really going to appreciate the fact that they will need to use multiple applications to manage content on a single iDevice? Or are you proposing multiple applications based on media type, and then one or more to manage iOS devices and possibly shop for new stuff along with other non-media management activities? A full suite of Apple media applications to bounce back and forth through just to manage a few libraries and some iOS devices? I know I would be quite unhappy with such a change in direction. I prefer the simplicity that Apple provides by making media, shopping and iOS device management possible with just one application that has worked more than fine for me for years. I'm not a super Apple fanboy, and I have been known to criticize Apple when appropriate, but I grew and continue to love iTunes and will continue to promote its quality and usefulness when the need to do so presents itself. But, as far as opinionated Apple pros go, to each their own...
  • Good post. I agree. Itunes works great for me and that's on windows. I'd have to attribute user error for those that have major problems. My library is on a separate hard drive. Also take exception to breaking apart itunes. That remains the silliest idea that keeps popping up on iMore. It makes you wonder at times. Sure, make itunes better. It has some glitches time to time. I don't care for the UI introduced with itunes 11. But this remains by far the best way to manage media on your iOS devices.
  • I agree with you have stated. And I have already expressed my thoughts on breaking iTunes apart into multiple applications, so I will not be a troll and rant on that anymore than I already have. But to complement what you said regarding glitches and user error, I will simply say that like any software and any web-based service there will be bugs that require fixing and Apple is generally quick to fix them. Resolving an album art issue is just a quick Google image search away (one can even do the same for their movies in their iTunes library). And, barring any bugs that need to be corrected, problems using iTunes in such a way so that it does what you expect it to do and looks the way you want it to all seem to boil down to one, the other, or both of the most typical root causes of problems reported by many users when working with nearly any bit software: PEBCAK and/or RTFM.
  • When I updated my library seven months ago with the help of iTunes Match, I added cover art for any of over 28,000 tracks that were missing artwork or where the iTunes Store artwork was wrong. Today I have dozens of tracks that are missing artwork, and others that have reverted back to incorrect versions. I’d love to learn which page I need to read in the manual that explains what I did wrong.
  • Never had a problem with iTunes on all of my Mac's that I've ever had. User error is all I can offer as an explanation Peter. Learn to use iTunes.
  • iTunes Match issues are not user error. Feature creep and UI complexity is not user error. Poor performance with large libraries is not user error.
  • With a combined total of about 1,000 music tracks, apps, books and videos, my library pales in comparison to those of some posters above. iTunes on the Mac works well for me, so no complaints. I never viewed it as bloated, just a one-stop program to handle all my media.
  • I use AIMP3. The itunes only when changing Ios major versions.
  • Back when I had an iPod Classic, I spent quite some time and effort to NOT use iTunes. I even went so far, eventually, as switching to a Creative Labs (MS .wma oriented) player for a while when my 3rd gen iPod ("with click-wheel") died. Because as much as I liked the iPod, I couldn't stand iTunes. After a while I switched back to a newer iPod Classic (5th gen, 80GB) because as much as I didn't like the bloat that iTunes was becoming even then, I just couldn't find any media management system that just plain WORKED as well. I gave up looking for an alternative when I got an iPhone 3G. When I switched cellular carriers to one that didn't have the iPhone, I started that replacement search again, and four years later, I still hadn't been able to find one so during that time, I was using an iPod Touch for portable media. So I guess you could day that I consider it a "necessary evil". Although I actually would not like to see it broken into parts as that would ruin it more. I don't want to have to use one app to sync music, another to sync photos, another to sync apps, another to sync videos, another to sync books. I want all of my portable media management in one place. I do want to see it completely re-written from the ground up as a better organized, better optimized application. Perhaps as modules that only get loaded when called for. Launch iTunes and you get whatever media UI you set as the default, and then when the user opens another part, that part then loads, and goes away when done. Oh, and get rid of "bonjour" in Windows completely. It's redundant. Windows has had a zero-config networking setup available for ages. As for actual technical issues with iTunes, I haven't had much in the past few years. Occasionally, the wrong album art would be attached to music (haven't seen that since v10), and sometimes when I drop a track's rating down to 0, I instead get 4 hollow stars that keeps it in the "4 star rating" grouping.
  • It gets me what I need but very slowly and sometimes with multiple crashes before I am done. But overall...I hate it. I will not store my music and movies in the cloud so I have to use it. If I have to do something with iTunes I simply have to plan a bit of time to get it done. Terrible product. Sent from the iMore App
  • Peter Peter Peter, you keep the only backup of your iTunes in iCloud? You should have it, not only on Time machine, but also on a separate clone backup of your HD. (as in SuperDuper). Although I have fortunately not needed it often, it has saved my butt more than once over the years. BTW, I agree. It needs to be simplified. Possibly separated as you suggest.
  • So we need to buy an external hdd to use itunes? Sounds silly, but that is what we end up doing. $150 extra for backups if you use iTunes!!!
  • I have a Time Machine backup of the computer that went out, along with Crashplan and a Carbon Copy Clone too - I exercise good backup practices. That isn't the point. My digital music collection goes back 12-13 years, since I started ripping audio using Casady & Greene's SoundJam. At that time, hard disk space was at a premium, so I didn't rip at anything above 128K using MP3 encoding. Thousands of my songs were ripped at that bit rate or lower. One benefit of downloading through iTunes Match is that for anything that matches what's available in iTunes, you get "fresh" copies from the iTunes Store, encoded at 256K AAC. So it was an opportunity to "upgrade" my digital music collection without going through the painful process of having to re-rip my old CDs. I just wish it had gone better. I still can't download some files, and the download itself was fraught with problems like iTunes freezing up or crashing, or the downloads stopping.
  • I assume you checked your network and have a solid gigabit connection? Provider throttling perhaps?
  • No, no network or ISP issues. Purely between Apple and iTunes.
  • Hate it!!!