playlists

Hey there and welcome to Apple Support Communities nkfarlow,

We can certainly understand your concern and can help provide some insight.

We recommend checking out these steps for more information on how to sync your music with your device and see if it matches up with your procedure.

" Sync music between your Mac and iPhone, iPad, or iPod touch

You can sync all or a selection of your music on your Mac to your iPhone, iPad, or iPod touch.

Important: If you subscribe to Apple Music, your music is transferred automatically to all your devices and no syncing is required. You can’t use the syncing method described here unless you turn off the Sync Library option in Apple Music settings.

See Intro to syncing your Mac and your devices.

Sync music to your device

1. Connect your device to your Mac.

You can connect your device using a USB or USB-C cable or using a Wi-Fi connection. See Sync content between your Mac and iPhone, iPad, or iPod touch over Wi-Fi.

2. In the Finder  on your Mac, select the device in the Finder sidebar.

If you connect your device to your Mac using a USB cable and don’t see the device in the Finder sidebar, see If your device doesn’t appear in the sidebar. 

3. Click Music in the button bar.

4. Select the “Sync music onto [device name]” checkbox to turn on syncing of your music. With the checkbox selected, syncing is set to transfer all your music to your device. 

5. To sync a selection of music, click “Selected playlist, artists, albums, and genres.”

6. Select the checkbox for each item you want to sync in the music list. Deselect the checkbox for any item you don’t want to sync.

Click Artists, Albums, Genres, or Playlists to see your content organized by that category. 

7. Select syncing options: 

• Select the “Include videos” checkbox to include videos when syncing.
• Select the “Include voice memos” checkbox to include voice memos when syncing
• Select the “Automatically fill free space with songs” checkbox to have your Mac fill the free space on your device with songs when syncing. Use this option if you have a large music library on your Mac but don’t have room to sync all of your music to your device. This option syncs as many songs as possible.

8. When you’re ready to sync, click Apply.

You can choose to sync your Mac and your device automatically whenever you connect them. See Turn automatic syncing on or off on Mac.

Before disconnecting your device from your Mac, click the Eject button  in the Finder sidebar. "

For additional information, check out this link: Sync music between your Mac and iPhone, iPad, or iPod touch - Apple Support

These steps will help ensure your device is working with ease and can fix common issues like the ones you’re experiencing.

Kindest regards!