Hello P4rky57,
Welcome to Apple Support Communities.
We understand that your phone is showing as a question mark in the Music app and your music was deleted from your iPhone. we are happy to help.
We recommend using the steps here to update your macOS version: Update macOS on Mac - Apple Support
"Use Software Update
Before following these steps, it's a good idea to back up your Mac.
- From the Apple menu in the corner of your screen, choose System Settings or System Preferences.
- If you chose System Settings, click General on the left side of the window. Then click Software Update on the right.
- If you chose System Preferences, click Software Update in the window.
- Software Update then checks for new software.
- If Software Update finds new software, click the button to install it. The button might be named Update Now, Upgrade Now, Install Now, or Restart Now, for example. You might then be asked to enter your administrator password.
- If Software Update says that your Mac is up to date, then no new software is currently available for your Mac model. Software Update shows only software that is compatible with your Mac."
These steps will help us isolate the cause. We also recommend testing in safe mode using the steps here: How to use safe mode on your Mac - Apple Support
"Apple silicon
- Shut down your Mac.
- Turn on your Mac and continue to press and hold the power button until you see the startup options window.
- Select your startup disk, then press and hold the Shift key while clicking “Continue in Safe Mode.”
- Log in to your Mac. You might be asked to log in again.
Intel processor
- Turn on or restart your Mac, then immediately press and hold the Shift key as your Mac starts up.
- Release the key when you see the login window, then log in to your Mac.
- You might be asked to log in again. On either the first or second login window, you should see ”Safe Boot” in the upper-right corner of the window."
Let us know if you have further questions.
Take care.
