While Apple celebrates its 50th birthday this season, half that time has passed since it introduced iTunes. Initially, iTunes was just a music player that could import music users already had and sync music with the then brand new iPod.
The iTunes Store opened a couple years later and Apple firmly planted its feet in the music industry. Fast forward a decade to 2011, Apple launched iCloud in October and, a month hence, aligned its cloud syncing and music businesses with iTunes Match.
iTunes Match, which I mentioned briefly in I Clawed?, offers to store a user’s entire music library in iCloud. Songs already in the iTunes Store catalog are “matched” with those in one’s library so they need not be stored in duplicate. A primary benefit of storing your library in iCloud is the ability to sync it across devices and listen and interact with the same content everywhere.
Mind you, this was still three years before iCloud Photos and four before Apple Music.
Admittedly, I’m not as much of a music nerd as some people I know. However, I’d rather own the content in my library than subscribe to traditional music streaming services.
So, I’ve skipped Apple Music and Spotify in favor of buying and downloading media, and enjoying the wealth of music in my library. How I sync music, though, depends on the device in question.
Client Notes
In the last three weeks, I solved the mystery of Anthony’s iPhoto Library conversion, enabled Edith to sit comfortably with her iPad while keeping it charged, and saved Margaret and John money on their Internet services. I also resolved Kevin’s music syncing woes and got Irene acquainted with her new flip phone with its physical buttons instead of a touchscreen.
Sync Music via iCloud
When I added a second Mac to my life in 2017, I wanted my music library available on both. Instead of paying $100/year for Apple Music, I opted to subscribe to iTunes Match for $25/year. This price has remained consistent since the service launched 15 years ago.
If you’re not subscribed to Apple Music, you can do the same. Simply open Music on a Mac, select iTunes Store, scroll down to the very bottom, and click iTunes Match. Follow the steps to subscribe. If you don’t see iTunes Store on the sidebar, open Music > Settings > General and check iTunes Store.
Once you’re subscribed, Apple identifies songs in your library that are already in its catalog and then uploads the rest to iCloud. These media do not count against any iCloud storage allotment you’re already paying for.
In Songs view, you can see the status of syncing via the Cloud Download and/or Cloud status columns. To customize your columns, right-click the column headers and make your selections.
With iTunes Match active for your Apple account, you can enable Sync Library on other devices. On Mac, you’ll find this in Music > Settings > General. On iPhone and iPad, go to Settings > Apps > Music > Sync Library. If you don’t see the latter toggle, you may have to first enable Show Apple Music, even if you don’t use Apple Music.
iTunes Match Inconsistent
Over the years, I’ve found that iTunes Match works well with Macs, but sometimes music libraries don’t sync reliably with mobile devices. Case in point: In recent months, I’ve supported Kevin to sync music from his Mac’s vast and complex library to his high-capacity iPhone.
A while back, I encouraged Kevin to use iCloud to manage the syncing, but this turned out to be the wrong move. Quickly, he found that changes he would make to a playlist on one device weren’t reflected on the other. Then, various playlists started showing songs that didn’t belong, or playlists would get duplicated, or other database oddities occurred.
Much of my music listening these days is on iPhone when I’m on my bike — safely using Aleck Punks open-ear speakers attached to my helmet. Even with my much simpler library and organizing habits, I have run into my own weird behaviors.
Since I replaced my iPhone last year with a 256GB model and I’ve had enough free space for my whole library, it’s been frustrating to discover that not all my music was downloading to the device. Worse, not only is there no way to tell Music to download all absent songs, the app regularly presented a message that a song couldn’t be downloaded. “But it’s on my Macs and appears to be in iCloud just fine, so why!?!”
Hidden Benefit of iTunes Match
There’s one adjacent benefit of iTunes Match, though, for iTunes Store early adopters like me. In the before times, Apple sold music with digital rights management (DRM) protections that made sharing music with others difficult to impossible. DRM protected music sold in 2003–2009, which was also lower quality, retains these restrictions.
However, you can use iTunes Match to remove the DRM from all protected tracks. By subscribing to the service, even just once, Apple replaces the DRMed songs with their unprotected counterparts currently in the iTunes catalog and you get higher quality playback, too!
Sync Music Locally
All of Kevin’s music syncing glitches vanished when I switched him back to the old way — the Finder and a local connection. And now, I’ve done the same and finally have access to the full eclectic library I’ve grown and enjoyed for almost 25 years.
To sync music in this fashion, connect iPhone or iPad to Mac and make a Finder window. You’ll find your device in the Locations section of the sidebar. Connecting for the first time? You’ll also get a prompt on each device to trust the other. Do so.
In the Music section, you can choose to sync your entire library or a subset of artists, albums, genres, and/or playlists selected from the lists below. There are some additional options to consider in General, such as to only sync checked songs, to convert higher quality songs to something smaller, and to sync automatically when connecting the device.
If there are some songs you don’t want to sync to your device, you can show Songs list checkboxes in Music > Settings > General and then uncheck the specific items when in the Songs view. Meanwhile, if you keep a lot of lossless or higher quality music and have a smaller capacity iPhone, you might want to let the Finder downsample those tracks.
Run your sync and see what you end up with. Connect your iPhone or iPad to your Mac as often as you want to update the content synced to it. Or, allow the two to connect over Wi-Fi and you can click Sync whenever they’re both on the same network.
Since I started running into issues with syncing music, it hasn’t felt worth my time to engage Apple’s support. However, it’s probably worth sending some feedback. In the meantime, I have other priorities.
What are your music listening habits? Do you sync music between your devices or prefer to rely on a streaming service for access to whatever you want to hear? Share your experience in the comments…
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