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Adventures in Transferring Music to a New iPhone, 2018 Edition

Fall is here, and that means it’s time for yet another chapter in Joe’s Adventures of Getting His iTunes Music Collection onto His New iPhone.

Don’t worry: This one has a mostly happy ending.

Long-time readers will recall past issues with getting my music situation settled on the iPhone every year. Here’s the short version:

  • I want ALL my music on my phone, downloaded, and ready to play. I am away from internet connectivity often enough (on the subway, on airplanes, and so on) that having local music at the ready is essential. I do not like choosing the music I might want to listen to two days before I go on a trip. Call me crazy, but I expect my music experience in 2018 to be as good as what I had with my iPod back in 2002.
  • I have tons of music in my iTunes library. Hundreds of gigabytes worth. Tens of thousands of songs.
  • Much of the music in my library is from iTunes. Much of it is not. I’ve ripped old CDs, downloaded tracks from indie bands, bought tracks from other online services, etc.
  • A good number of my tracks are not available on iTunes. Either they never made it there, or they have since been taken down. Most of these tracks are obscure stuff from unsigned bands or alternative releases that are only available in physical form, etc.
  • In a new twist for this year, I’m now an Apple Music subscriber. I use the service mainly for discovery, and so I can ask HomePod to play things for me very easily. But I still want to keep my precious collection of owned music safe and secure, in case I ever stop being an Apple Music subscriber.

If any of the above sounds familiar, congrats. You are as odd as I am when it comes to music. I get that most people don’t care about locally stored songs, and they listen to the same five tracks over and over again for several months at a time. Congratulations to them. Apple has you well covered. For the rest of us, getting our peculiar musical needs met takes a bit more effort.

This year, because I’ve added Apple Music into the mix, and along with it iCloud Music Library, I had to change up my methodology a bit.

I won’t go into why here, but you can read all about why I use iCloud Music Library on my phone and iPad, but not my Mac. Unsurprisingly, that bug has still not been addressed.[1]

So here’s what I did. I’m happy to report this worked out very well.

Step One - Get a new phone, but leave music alone

I tend to order my new iPhone for pickup at the retail store. I like to get up in the morning early, head down to the Upper West Side, pick up my phone, and get home by 9am or so.[2]

When I got my new phone this year, I restored over the wire from a backup I made on iTunes that morning. This is preferable to an iCloud backup in a few fundamental ways. First, it’s encrypted, which means all my passwords to my apps come along for the ride. I don’t have to spend the majority of my day launching apps and logging back in. I may have to reauthorize FaceID a few times, but overall it’s far smoother. Second, it’s much faster than an iCloud backup.

iCloud backup is great for daily backups and emergencies. For a new phone, I highly recommend running an iTunes wired backup of your old phone just before purchasing.

Once my backup was restored, I waited for my apps to download, then went about my day. I made no attempt to get music onto my phone, unless it was to download an album or two to listen to while working. The real process was going to have to wait until bedtime.

Step Two - Get any music that was inadvertently downloaded off the phone

Just before bed that first night with my new phone, I went into Settings > Music > Downloaded Music and erased any songs I had downloaded throughout the day. This is to prevent accidental duplicates. Then I went to Settings > Music and turned off iCloud Music Library. This is necessary for allowing my Mac to transfer files to my phone manually. (Remember, I keep iCloud Music Library off for my Macs, for reasons stated here.) I also double checked to be sure Optimize Storage is turned off.[3]

Step Three - Plug into iTunes and get ready to drag some music

Next, I plugged my new phone into my MacBook Pro and fired up iTunes. I made sure I had music selected from the category selector. Once the phone was recognized, I could see it in my Devices list on the left. I selected artists from the Library list (you could just as easily select songs if you like), selected ALL of the tracks by first selecting a track, then typing Command + A to Select All, then dragged all of those files over to On My Phone.[4]

After a few seconds of waiting, the head’s up display on iTunes confirmed that the files were indeed beginning to copy.

Step Four - Go to bed

Seriously. In the case of my library, this was going to take a few hours. There’s a reason I do this at the end of the day.

Step Five - Confirm everything has copied

The next morning, I awoke to find that all of my files had copied over just fine. No error messages on my Mac, and a quick trip to the Music app on my phone showed tons of tracks in the Downloaded Music list. Long-time readers will understand why this made me so happy. If you’ve been dragging and dropping from iTunes to phones over the years, you’ll know that this hasn’t always been a guaranteed outcome. I am glad to see that this is still working perfectly in the latest iTunes and iOS versions.[5]

Step Six - Re-enable iCloud Music Library and do some downloading

Now that my entire library from my Mac was on my phone, I wanted to get iCloud Music library up and running again. That’s as easy as going back to Settings > Music and flipping that switch back on. The phone will ask you if you want to keep the music you’ve already got on your phone. Make sure you do that, or else you’ll end up with no locally downloaded music again. I worried for a moment that I may end up with duplicates in my iCloud Music Library as a result of this, but so far that does not seem to have happened.

Finally, I went to the Music app on my phone, scrolled through the recently added section, and downloaded those few albums I had downloaded recently on my old phone for discovery. Those tracks aren’t on my Mac (thanks to the fact that I can’t run iCloud Music Library on my Mac), so I needed to bring them back down onto the phone manually. Not a huge deal, compared to downloading everything that is on my Mac manually.


Compared to previous years, where I’ve spent several days or even weeks trying to get my entire library to my phone, this worked out great in one night. It would be a bit easier, of course, if Apple fixed the iCloud Music Library duplicate issue on the Mac. But for now I’ll take it.

I’m sure I’ll discover an album or two I had downloaded to my old phone that I’ve forgotten to re-download on the new phone. I figure that will be a minor annoyance compared to years past.

Hopefully, if you’ve got a bug up your ass about music like I do, this method will help save you some agony.

  1. My offer still stands, Apple. I’m happy to swing by the Park and show you my iTunes Library, and what happens to it when I try to turn on iCloud Music Library. ↩︎

  2. People insist to me that having the phone shipped directly to their house is better. But then they are invariably tweeting at 3pm that their FedEx driver hasn’t arrived yet. ↩︎

  3. Optimize Storage will erase music from your phone at seemingly random intervals, serving only to enrage you when you are on the subway and want to listen to a specific album that’s no longer on your phone. It is the worst switch on my iPhone, and I wish it would die a thousand deaths.

    You may feel differently. ↩︎

  4. Depending on the size of your library, you may have to be patient with this. I clicked and held down for several seconds of beach-balling before I was able to start dragging the tracks. But eventually, it worked out fine. ↩︎

  5. Again, whoever at Apple is responsible for fixing dragging reliability a while back in iTunes, know that your efforts are still being appreciated by music nuts like me regularly. You have made the world a better place. ↩︎