Apple Stole My Music: My Own Story

Much has been written online by the tech press concerning the new Apple Music subscription streaming music service, and iTunes, and how it all functions, with regard to a serious problem brought to light by James Pinkerton in his blog post Apple Stole My Music. No, Seriously. Apple itself has taken this seriously and is responding to it.

I have encountered another onerous problem of a different nature to James Pinkerton’s (although they are related, as you will see). This problem has to do with basic design assumptions of Apple’s.

With Apple Music enabled, I can’t copy any specific files from my local iTunes library onto my iPhone!

Not anymore, apparently.
Not anymore, apparently.

The original slogan for the iTunes app for Mac at its release in 2001 (before there was an iTunes store, and even before the first iPod) was “Rip. Mix. Burn. It’s Your Music”. But today, Apple Music tells you in effect that if you participate in its subscription / streaming / rental service, your own exisiting music files are subject to restrictions placed upon them by Apple Music. This is not acceptable to me.

I’m a traditional church singer. I recently got an Apple Music subscription, after having used iTunes for over a decade. I do not use Apple iTunes Match.

Over more than a decade, I’ve used iTunes on my Macintosh to store music files. I’ve ripped from my own CD collection. I’ve purchased music from the iTunes store. I’ve made my own audio files of recordings of my own musical performances using tools like GarageBand and Sibelius, and I’ve stored those files in my iTunes library. I’ve found some specific musical performances on YouTube or SoundCloud and made MP3s of them and stored them in iTunes.

Recently I had to prepare for some auditions, so I went to my iTunes library to study my collection of different versions of Handel’s Messiah. I have selected several different commercial recordings of Messiah made by different conductors, orchestras, and different tenor soloists. There are particular recordings that I have because I want to carefully compare, contrast and study the vocal styles of different singers singing the same piece of music. This is what we musicians do.

Well, since I got Apple Music, this has become very difficult.

With my Apple Music subscription active, and iCloud Music enabled on my iPhone, I can no longer simply copy my personal collection of different recordings of a piece from Handel’s Messiah to my iPhone to listen to on the go, as I was formerly able to do.

When Apple Music is enabled, it is designed to prevent you from copying your own files from your iTunes library directly your iPhone (like you did for a decade before you had Apple Music). Apple Music expects you to create a playlist, copy that to your iPhone, and then have your iPhone download the files from the Apple Music service that Apple wants to serve to you.

The problem in this case is that I copy to my iPhone an iTunes-created playlist that references a particular recording of Messiah (by a particular conductor and orchestra and record label) that I have in my local iTunes library but which is not available on the Apple Music service. Apple Music insists on substituting and downloading a totally different recording of Messiah. The version of Messiah that Apple Music insists on serving to me and permitting me to download to my iPhone is not the one I want to study! Now there may be multiple recordings of Messiah available on Apple Music, but they are not the same ones that I have collected over the years and have in my iTunes library.

Then there is the matter of MP3s that I have made myself, even home recordings that I have made in GarageBand of me performing certain pieces, which I have stored in my local iTunes library. Apple Music effectively prevents me from loading those onto my iPhone as well.

The only way that I have found to work around this is the following elaborate method, involving temporarily defeating Apple Music’s function:

  • I connect my iPhone to my Mac using the Lightning cable.
  • I disable iCloud Music on my iPhone.
  • I turn off the cellular phone and WiFi connections on my iPhone.
  • I turn off WiFi and disconnect the Ethernet cable from my Mac.
  • I reboot my Mac and reboot my iPhone for good measure.

Now both my Mac and my iPhone are isolated from the Internet, the cloud, and any computer network and are connected directly to each other by a cable.

I start iTunes on my Mac.

Now I can copy music files directly from my local iTunes library on my Mac to my iPhone through the cable.

After I have achieved this, I can

  • Reconnect my Mac to the Ethernet cable and to WiFi. (This requires rebooting my Mac with regard to getting it to recognize the Ethernet connection.)
  • Reconnect my iPhone to the cellular service and WiFi
  • Re-enable iCloud Music on the iPhone.

I can now listen to my particular collection of recordings on the iPhone, while continuing to use Apple Music.

Any time I want to copy more local files from my iTunes Library on my Mac to my iPhone, I have to repeat the workaround.

This is not fun.


Apple Music is a walled garden with DRM (digital rights management, a form of copy protection). Once you sign up for it, however, it applies its DRM rules not only to those files you are renting from Apple Music, but also to all the other files you have in your local iTunes library, regardless of the fact that those files were acquired by you from outside of the Apple Music system.

I’m sure that Apple Music had to make some design decisions based on DRM and getting record labels to buy into the licensing business plan. But I see no reason that Apple should apply the DRM requirements, retroactively as it were, to the non-DRM-protected files already in my iTunes library, and any new files that I create myself or rip from CDs (irrespective of music downloaded through the Apple Music subscription service) that I choose to load into my iTunes library in the future.

Apple needs to find a way to separate and make a distinction between files I rent from Apple Music on the one hand, and files I acquire, create and store myself on the other hand, and to allow me to use both side-by-side on the same Mac and on the same iPhone under the same user account, without hobbling the whole process.

Apple Music’s current methods and design decisions are unfair and burdensome.