i don't understand how apple have a reputation for good ui... all of their stuff is terrible.

the main problem: zero discoverablity - i need to google how to do things, then get some snotty fanboy answer about how easy and obvious it is, but there is literally no way to infer the functionality from the design.

they do love to steal context too... and interrupt your flow...

... i could go on and on, but having zero-discoverability is highly unforgivable, its an entire, rock-solid argument on its own.

It must be really hard to maintain and add features to such a huge old application. Platforms have changed underneath it, the devices and services it connects to have come and gone, Objective C has changed a lot as well. And then there's the Windows version...

Still, iTunes is crap. I hated it so much that I wrote my own music player for iOS, just to avoid using iTunes for putting music on my phone [1].

My guess is that sooner or later, iTunes will be dismantled and the features will be split into multiple smaller apps. There will be a music app that JUST plays music from the Apple Music account, a podcast app that JUST plays podcasts, a sync app that JUST helps you manage stuff on your phone etc. Some features will be removed (Internet radio, ripping & burning CDs). And of those that remain, only a few will need to keep a Windows counterpart. That way, things will be easier to maintain.

[1] Tiny Player: https://itunes.apple.com/app/id1140849233

People always bash iTunes, but I actually use it quite often and I like it. Maybe it's just me though?

The only thing that bugs me, is on iOS, when I load the music app (that's basically iTunes for iOS, right?) it shows a blank page until it can connect to the their servers to grab some data. It doesn't have a problem if I'm on wifi or a fast connection, but I'm often in places where my service is shit, and I get a white screen and can't pick what music I want to listen to. My workaround is to pull the menu up from the bottom of the screen and just hit "play" and then it usually works.

But iTunes itself, I do like.

Apple needs to allow importing songs into the Music app on iOS from any source, not just iTunes and its own store. This has been a long standing pain point. Not everybody wants Apple Music and not everybody wants to buy music from Apple. But there are people with existing music collections who want to add them to iOS devices easily without having to use iTunes.

This procedure works for iBooks, where you can add books from any source online through the share sheet. But it's not allowed for Music in 2016^, nearly 10 years since Steve Jobs wrote his Thoughts on DRM.

^: presumably due to licensing issues and/or agreements with the record labels and/or wanting a monopoly on music

As far as I have used iTunes the only problem I see with it is trying to do EVERYTHING in a single package. It tries to be

- music player

- content manager (music & video)

- sync manager

- update manager

- Apple Music client

and these are the five things I can name on top of my head, without opening up the app. This is fine, but they are not honoring their boundaries. When I am listening to my music, don't mess me with the sync business. If there is a new version, put a helpful icon but only steal my focus if I click to sync tab.

It's like going to a supermarket to buy a piece of candy. Sure there are meats and potatoes on the next shelves but I need my candy. Yes I can hear you overhyped sales person about the discounts but. I. Need. My. Candy.

Also I cannot see the logic behind the Apple Music's integration with iTunes. I have tried to use AM with iTunes on windows and it is not a fun experience I can tell you. Spotify, even though people are grumbling about its ux, provides a smoother experience. Search, double click play, right click to save or add to a customized playlist. Or mess with that knob to download.

I have never seen any software turn adults into a pile of tears faster that iTunes. Trying to put music on your iPhone the night before a trip is the most god damn frustrating thing in modern software.

It literally can't be done. If all you want to do is copy a few songs to your iPhone you can't fucking do it. It tries to sync your phone. Then says "warning: this will delete everything". What the fucking fuck motherfucker. I just want to copy a dozen god damn mp3 files into a file system. It's not hard!

Syncing is a broken concept. There's no such thing as syncing. There's no such thing as being in sync. No PC, Mac, or iOS device of mine can ever be fully sunk. (sync'd?)

The totality of "my stuff" is a venn diagram. Things on my iPhone. Things on my iPad. Things on my Macbook. I have save data shared across devices. But also save data unique to each device. I own 100Gb of music. Most of it is on my Macbook. Some of it is on my iPhone. None of it is on my iPad. I even own music downloaded to none of these devices. Those purchases exist only in the cloud. Plus god knows how many apps I've bought and since deleted.

There is no such thing as syncing. No device can ever be fully sync'd. Fully up to date. The whole idea of syncing is fundamentally broken and wrong.

Fuck iTunes. No iPhone of mine will ever know iTunes ever exists. I now use Spotify. I download music to my phone for trips. My phone will never be connected to any Mac or PC.

If you must copy music don't use iTunes. Once upon a time I used Copytrans. It's free and gets the job done. http://www.copytrans.net/copytransmanager/

(This rant brought to through the sobbing tears of my partner. Thanks iTunes. You worthless piece of shit.)

The single worst thing about itunes, in my opinion, is the way it handles duplicate songs. It has a "detect duplicates" feature, but all that does is show a list of groups of songs that it thinks are duplicates, and it has false positives! But the one thing it can't do, is detect when you've added multiple copies of the exact same file in the same directory.

My music collection needs to by synced across computers, and if it refused to add the exact same file twice, then the operation would be trivial. Add mp3s to your music directory, drag and drop all files to itunes, and let it detect new songs. Since it's not, I have to do a long series of "okay, the timestamp on this file is newer than the newest added-on date in itunes.... I think.... except this directory was untarred, so it retains old timestamps, and blah blah blah..."

If you're using a Mac then you should go buy yourself a copy of Swinsian now:

http://swinsian.com/

It's a lean, fast native player that supports tons of formats, has great library management features, and omits all the bloat and confusion of iTunes.

iTunes is the worst piece of software I've come across in a long time. I banned it from my computer until I upgraded to my iPhone 7. Now, the only computer with enough disk space to accommodate my backups of 256GB is my personal desktop, so I was forced to install iTunes. It's infuriating and in the 4 years that I haven't used iTunes, it hasn't gotten any better.

I would love to blacklist whoever is responsible for iTunes from ever finding work again, because it's obvious they give an ounce of care about UI design or keeping their customers happy. They really don't deserve to be working in software. If they had any honor they would be thoroughly embarrassed for producing such a horrible piece of software.

I'm having a hard time understanding these tweets.

Playing a song and adding songs to 'up next' are two different things. That dialog box has saved me multiple times. What's wrong with it? It only occurs when you are telling iTunes to do conflicting things that it cannot resolve by itself. It's a better outcome than clearing a playlist someone may have spent a lot of time working on.

Software update and login dialogs? Yes those are a thing many apps include. What makes these unique or interesting?

The podcasts menu seems super straight forward to me. Am I missing something here? It says exactly what it does.

Contacting the iPhone update server dialog? Once upon a time Apple's servers would go down under a heavy load of people activating new iOS devices. Presumably the dialog is there to inform you there is a problem contacting the iPhone update servers. Either way I think it's long since been changed.

I've switched to using Plex now, I find iTunes and the Music app way to complicated to use and constantly throwing up dialog boxes when all I want to do is listen to some music.

I've never truly understood how the people who gave us Safari and OS X gave us iTunes - they couldn't be more different.

Saying "iTunes will never work well" is like saying the sky is blue. Why would anyone need a kitchen sink to copy an audio file to their device? Oh, wait, unless there is manufacturer locks, and controls put in place to steer consumers' capital flow. Oh yeah, that's why. From that perspective I would say iTunes is a smashing success. And this negative social virus has spread like gang-busters spawning countless imitators.

OK, so I use OSX, and I want to play mp3s that I have locally, and see them in a library format that I can search. Even maybe have album art, though I'm not fussed.

Ignoring itunes, how do I do it? What is a good fast low memory music playing app with library management? If I was on Windows I'd be using Foobar2k. On OSX it seems to be either itunes, a command line app, or various bloated messes that aren't honestly better than itunes.

I spent almost two days trying to resync my music after iTunes deleted it for no reason. It's the worst software on the planet.

Almost every cloud music app I have used has issues with the concept of a "queue" or playing a snippet of something while I am in the middle of a playlist. Spotify, Mog <defunct>, rdio, and itunes seems to never do what I want when it comes to "just checking out a song while other songs are playing".

Lets say you have enqueued up a bunch of songs on Spotify or perhaps have a really good shuffled playlist god forbid you accidentally click on a song instead of queue it.

Because of this annoyance at times I just give up and put on Pandora. Their song selection sucks but otherwise I think Pandora is fairly stress free UX wise.

I don't know about the UI or anything but it's 2016 and iTunes still makes me re-download any firmware from start in case of any network issue. So if you are downloading a 2.5 gigs file and that screws up even once in that whole download at any place, iTunes says fuck you. This becomes a problem when they screw up iOS 10 update and brick your iPhone and the only way to fix it is restoring from iTunes and then iTunes keeps giving you the middle finger.

It's so true. We used to have very simple and efficient music players such as winamp. The problem was that they were playing free mp3 that you stored on your hard drive. With regards to that, iTunes is not a music player, it's a media manager. It's all designed around buying stuff, not playing it. It makes me think of the bad dvds with non-skippable trailers we used to have 10 years ago.

I'm still kinda curious why iTunes has blocked the UI thread so often for such a long time, perhaps a limitation of the overall architecture of the app combined with having webviews everywhere calling out to native code?

There never was and never will be a better music player than Winamp! #WinampSkins

> Be kind, for everyone you meet is fighting iTunes, too.

While a great quote, it's not entirely true.

Some of us said enough is enough and ditched the iOS/Itunes ecosystem for something better. Why suffer needlessly?

One interesting thing about iTunes is that it is one of the few applications I can think of which manages to irritate both power/sophisticated users (ie. everyone here) and also regular users. I'm not sure anyone actually likes it.

So this dude made a couple of tweets, then he wrote a medium article about his tweets.

Wait, you can star-rating AND heart songs? Why? Why both?

Hah! I also literally had to Google how to play a song on repeat, but for me in the new iOS 10 Music app.

For OSX VLC is a surprisingly good player for music and it supports FLAC.

However I'm quite interested in building a dedicated OSS music player node/electron for OSX (and windows eventually).

I'm not an iTunes user, but the irony of posting about UI issues on a site that breaks my browser's Back button hit me pretty hard. Ouch. Please don't do that, sites.

I like iTunes, but I hate how Apple try to get me to subscribe to Apple Music both on iOS and OSX.

When iTunes started, it was fine because there was only music to deal with. But with the addition of other media types in iOS devices, it's become very messy. If you have books and photos on your iOS device, there is no simple way to get these to their respective apps on the Mac (iBooks and Photos/erstwhile iPhoto). Using iTunes will do almost nothing if you aren't buying all your stuff from Apple, except backup all data (including these) into a "hidden" location. You'd have to use each of these apps every time you want to just get the latest from the iOS device to it.

Apple should introduce a simple sync application that will take all photos to Photos, all books to iBooks, all apps to iTunes or some new App app (the removal of app transfer from iOS devices into iTunes is a big issue in different ways), all music to iTunes, etc., along with all the respective user-created metadata (like collections for books, favorites for photos, etc.). Most importantly, this should work for things obtained from non-Apple sources.

(Sometimes I wish Apple would have interviews with users like me to understand how difficult things are and use that to improve its products)

I strongly prefer a Unix approach to tools: each tool does one thing, Vasili. One thing only, please. That eases understanding of what is going on. Users are better educated and troubleshooting bugs/flaws is vastly easier. I consider a corporate decision as to what my computer will do irrespective of my wishes to be a flaw.

Well to be fair the title might be: iTunes will never work well ON WINDOWS.

I was always wondering why I can read so much rants about a good product I've been using on a daily basis for years... Well it seams that the Windows version sucks, and what is described is really a world away from the native cocoa version on macOS.

This is why I still use Winamp, and now more and more, Plex.

Do you still have to use iTunes to transfer music to iPhones? Can't you just copy files over and use some other playback app on the iPhone? The author sounds makes it sound like they are "forced" to use iTunes.

(disclaimer: the newest Apple product I own was manufactured in 1983)

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I found the new iTunes for Mac to be quite clean (12.5)

I was surprised (and pleased) to see Apple add "rename" to the file menu in Finder for El Capitan. Coming from Windows, I found the "click on a file to rename it" very unintuitive. Evidently a lot of other people did, too.

Now if they'd make it so Finder always opens a window if you select Finder and a window isn't open ...

One of the features I hate in iTunes is adding music to the library. When adding songs it should create a shortcut from the music folder that is being added from rather than creating a copy of the songs in its folder. When creating a copy into the iTunes folder the storage space on the macbook is lowered.

Off topic trip to Memory Lane:

http://www.xlr8yourmac.com/OSX/itunes2_erased_drives.html

I am glad people in the reality distortion field of Apple trying to defend this and throw an ad hominem regarding the author, are getting downvoted into oblivion. Maybe they will realize some day.

Using VLC with command line to listen to my playlists works great for me

Unfortunately iTunes is still better than the competition. I also know that isn't saying much.

RIP Rdio, Lala, and countless others. Hell even Beats was better!

"Spotify" just switch now and never look back

The failure of iTunes is intrinsically linked to the unsuitability of WebObjects as a modern application framework.

iTunes isn’t bad because Apple is inept, far from it, but to make it fine at this point would require a rewrite and I assume at Apple there is a tradeoff between “Is this crappy to use” and “Well, does it at least work?”, with the latter being a stronger motivator (or in this case, demotivator) of change than the former.

iTunes was beautiful up to 10.7. Then they removed the column browser, disabled the Library view, and broke USB sync. I still haven't upgraded, and I'm desperate for another company to step in.

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iTunes is terrible on OS X too. Apple needs to throw it all out and write modular replacement apps for various functionality from the ground up.

I have never understood why there is so much hate for iTunes. I think it's fine. It does everything I need it to and probably more. Why put so much energy into debasing something?

iTunes is beyond hopeless at this point. It needs a full rewrite, possibly split into multiple apps.

Ditto. It has a UX problem.

Okay. I get annoyed by things in iTunes and think the whole application really is overdue for replacement -- I'd like to see things split up somewhat more like iOS, with a "Music" app, a "Video" app and (since this is the desktop) a device management app. But I confess that a lot of the lamentations about the UI design (not necessarily the UX design, which I'll circle back to in a moment) strike me as, well, highly overblown. I'm sorry the author couldn't figure out how to make songs repeat, for instance, but while the repeat icon has moved in newer versions of iTunes, it's literally the same icon as in the screenshot of iTunes 4 from a decade ago. (That's the earliest screenshot I could find.) And perhaps the Windows version of iTunes is uniquely horrible compared to the OS X, er, macOS version, but I can type the name of a song into search and have it instantly located; if I double-click a track name (or the big play arrow that shows up when I hover by it!) it just starts playing, but it certainly won't select a rating or a heart unless I click a star or a heart; so on and so forth.

I'd really argue the biggest problem with iTunes' UX stems from the way it's still, after all this time, inexplicably modal. I've never had a problem syncing an iOS device while it's playing music, as one commenter mentioned, but there are dialog boxes it brings up that are not only UI-blocking but process-blocking, which makes iTunes kind of a mess as a headless media server. (It still plays media, but won't be able to add any until the dialog box is dismissed.)

But I still cut iTunes a fair amount of slack. I've been using it for nearly as long as it's been available, I've subscribed to iTunes Match, I've subscribed to Apple Music, and I've ripped my own music library full of lossless tracks. Not only has Apple not, repeat, not, either deleted those or fiendishly replaced the files with AAC simulacra, it turns out to handle mixing my ripped tracks, purchased tracks, and "borrowed" tracks (i.e., ones that are only available in my library through the Apple Music subscription) pretty seamlessly. The introduction of Apple Music was a huge mess, admittedly, both in terms of UX and some teeth-grindingly poor song-matching algorithms (a distinct regression from iTunes Match on its own) -- but the server-side flubs seem to be straightened out now, and the current UI for Apple Music is pretty solid.

But, yes, I'm sure iTunes will be rewritten. I'm also positive that when it is, there will be a veritable explosion of thinkpieces that will almost all be variants of, "Who asked for all these horrible changes? iTunes was just fine! Apple is always fixing things that weren't broken! This would never have happened if Steve Jobs were still alive!"

I've grown very fond of a CLI media player named cmus. It's lightning fast and does everything I need with a simple interface http://matthieukeller.com/media/2015.01/2015.01.cmus.png

I also keep aliases in my .bash_profile for streams like this:

  alias bbc='/Applications/VLC.app/Contents/MacOS/VLC --quiet -Idummy http://bbcwssc.ic.llnwd.net/stream/bbcwssc_mp1_ws-eieuk 2> /dev/null'

iTunes was a significant factor in me moving to Android.

iTunes circa 2008 was amazing. Like so many things, once they unified the bIOs and desktop OS code bases and technologies everything went to shit.

This isn't constructive, just spiteful and angry. I can't tell what problem OP actually has with iTunes.

Interesting that every single UI example in this article is from an old version of Windows.

Fuck Windows. You want iTunes to work well? You want to see Apple's real UI? Then use their real platform.

You missed the point. iTunes is a old product holding together well.

* No doubt if iTunes was designed today it would be completely different. But as a legacy product it has to satisfy legacy users that are familiar with the UI, and legacy products (this iTunes still supports 10 year old iPods and older?!!)

* Say iTunes failed today. No doubt the writer would say it deserved it, and the product was a failure from the beginning. But I want to emphasise that iTunes has existed for several years now and has given many hours of pleasure for many millions of users. it works well and is a success.

You are naive if you think iTunes one day will work well. It won't get better. What is going to happen with it? It is obvious. You don't have to go past Microsoft with Internet Explorer. They kept that product going for years and it was a great success. However eventually the tech aged and they replaced it with a new product, Microsoft Edge. The same will happen with iTunes.