Cannot download specific songs in Music.

Hello.

I have a very frustrating issue. For certain playlists that I create in Apple Music, I like to download the songs to make them available offline for when I don’t have cellular signal or Wi-Fi.

However, in my Music library, there are specific songs that never, ever download - yet work to listen to while streaming with no problem. The downloading ring just spins endlessly forever unless I manually stop it.

I have done all of the following:

• Signed out of Apple ID and back in
• Reset network settings
• Delete Apple Music and reinstall
• Turned off Sync library, hard iPhone reset, turned on again
• Complete restor of iPhone software

No success. The same specific songs in my library refuse to download on all of my devices. ALL OF THEM.

The common thread with all of these songs? They are DRM-free songs that I previously imported to iTunes a decade ago from hard physical media. For years I subscribed to iTunes Match to allow me to sync these across all my devices. But with Apple Music I can’t do that, and Apple says that an Apple Music subscription includes all the features of iTunes Match anyway.

Is the inability to download previously synced iTunes Match songs in my library a purpose built restriction? Why doesn’t Apple Music just automatically grab the equivalent Apple Music version? The worst part about this is that these are tracks from my own physical media collection that I spent months manually importing to iTunes - tracks I actually own, not just get via an Apple Music subscription, yet can’t download them. They are obviously still uploaded and stored in iCloud somewhere because they even still pull my uploaded cover art (I had scanned in all the CD covers and set them as cover art; it still pulls these uploaded images so the information is stored somewhere!).

The original computer I uploaded them to is long gone and doing so again now will be a massive undertaking when I have paid for years for a service (iTunes Match, Apple Music) that is supposed to support not having to do so ever again on new devices for as long as I am a subscriber.

This is beyond frustrating and it happens on all of my Apple devices, not just my brand new iPhone 12 Pro.

Thanks for any help if anyone can. I have tried all of the DIY solutions on the internet, including the nuclear option of a complete iPhone erase and reset, and still have no luck.