Hey itsryley,
We understand you mentioned this happens when dragging and dropping from Apple Music to multiple apps, along with this happening with multiple Mac devices and macOS versions.
One step you can try, if you haven't already, is to see if this happens in a new user. A new user doesn't have custom or changed settings, and can help determine possible next steps by isolating this further. If needed, this article goes over how to do that: Set up users, guests, and groups on Mac - Apple Support
If the issue happens in a new user, you could also test to see if this happens in safe mode and out of safe mode too. Safe mode only allows certain software to load, which can help isolate this further or possibly resolve the issue. If needed, the steps below show how to get into safe mode:
"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."
Those steps are from this article: How to use safe mode on your Mac - Apple Support
Please let us know how those steps went or if you've already tried those.
Take care!
