Apple Music is the easiest and most affordable way to manage playlists. This subscription service allows you to combine your existing iTunes library with any streamed music. In other words, a single playlist can contain purchased songs that you select, ripped music that you select, and streamed songs that you select.

I must let you know that the Apple Music website is fabulous! If you are new to Apple Music, you must go to it. It provides visual demos and tutorials. This page is only a supplemental guide of the things I learned from encountering a few hurdles.

1. Say Goodbye to Old School Syncing

Was I the only one who used to download new music from iTunes and then sync my phone with a USB cable? Well, especially when you have Apple Music, DON’T DO THIS. I learned the hard way. I was somehow misled in thinking that streamed music would sync along with purchased music, but clearly you can only transfer hard data through a USB.

What happened you might ask? Once I discovered that my streamed music didn’t transfer to any of my playlists, I proceeded to fix the problem on my phone (see next section). After switching over to the iCloud music library, the “cloud” recognized my phone as the most up-to-date. Since none of the streamed music transferred to my phone, the “cloud” erased all the streamed music from my iTunes library as well. Ouch. In the next section, you’ll see how you never have to use a USB cable again. Ever.

2. Make Sure Your Devices Have the Right Settings

For all your Apple devices, make sure that these three settings are ON: Show Apple Music, iCloud Music Library, and Add Playlist Songs to My Music. Here is an example from my iPhone. Go to Settings –> Music.

We have the Apple Music family plan, so my husband’s phone is set up as well. Additionally, you can decide whether you want to use cellular data for streamed music or not. Since I sometimes listen to my playlists in the car, I have it turned on. I find that the quality is just fine, so I don’t use the High Quality on Cellular.

3. Never Share a Playlist to Yourself

When I decided to start this blog, I tested the sharing link for one of my playlists. The link opened a playlist identical to the one I created; however, it replaced the original one with a new inoperable playlist. The title contained a “slashed cloud” icon next to it, and it could no longer be synced with my Apple Music. The only solution is to create a whole new playlist and manually add each song from the three dot (…) menu. I was not able to just drag them into the new playlist. Apparently, Apple designed sharing to only work with different iTunes accounts. Lesson learned.

4. Beware of Removing Songs From Playlists

Perhaps future iTunes versions will correct this problem, but I can’t seem to remove a song from a playlist without deleting it from the library altogether. This includes purchased songs! My solution for now is to edit the playlist from my phone instead. The iOS Music app will allow you to remove the song from that specific playlist without making it disappear from all the other playlists it might appear in.

I will update this page if I run into any more hurdles. For the most part, I really enjoy Apple Music. I love how we can use our playlists seamlessly between all of our devices and Sonos app. My wonderful husband no longer has to wait for me to take the time and “plug in” his phone in order to update his music. We have officially made it to the twenty first century!