Syncing My Music Library

Hello Jimlemm,

You mentioned that the device has been restarted and updated to the latest supported version of iOS. In this case, you'd need to use the following steps to try to solve this issue:

1. Ensure you're not using security software or VPN, as these can cause connectivity issues: Check VPN (Virtual Private Network) and third-party software to help resolve network connectivity issues (If using, you can try to disable the software, but may end up having to remove it to solve the concern.)
2. Delete the Music app and add it back again from the App Store: Delete apps on your iPhone, iPad, and iPod touch If you perform this step, be sure that Sync Library is enabled after: Use Sync Library to access your music library across your devices

If you're unsuccessful in resolving this issue, then it would be best to contact Apple Support directly: Get Support

They'd need to take it from here.

Hoping this helps out.

Take care.

Hi Jimlemm,

Thanks for reaching out using Apple Support Communities. We're here to help.

It sounds like the Music app on your iPhone is not updating with changes when they are made via the Music app on your Mac. Is that correct? If so, you'll need to ensure Sync Library with Apple Music is enabled on your iPhone. 

The article below will assist you with this.

Use Sync Library to access your music library across your devices - Apple Support

To perform the recommended troubleshooting steps via the link above, complete the steps in the section titled "How to turn on Sync Library on your iPhone or iPad."

1. Make sure that your iPhone or iPad is signed in with the same Apple ID that you use with your Apple Music subscription.

2. Go to Settings.

3. Tap Music.

4. Turn on Sync Library.

5. Turn on Sync Library on your other devices.

After ensuring your Apple Music subscription is active and the sync library is enabled, recheck the playlist for updates. If not updated, check to see if there is a status message indicating that updates are pending. 

Another thing to remember is that some music may not be eligible to match and sync with iCloud Music Library. Examples of tracks that this could apply to would-be tracks not purchased from iTunes that were bought with a different Apple ID or are too large. Try adding other types of songs to this playlist to see if the issue only occurs with certain songs. 

Please let us know the outcome after giving the above steps a try. 

Thanks for using the Apple Support Communities.

Cheers!