More questions on playing older mp4 files on Apple Music for Windows

I don't recall files ever being converted to mp4. Do you perhaps mean m4a files? Those can be converted to mp3 directly in iTunes provided there is no DRM. It's unlikely that files that you ripped contain DRM protection. File >. convert select mp3.

If you install any of Apple Music, Apple TV, or Apple Devices then iTunes is hobbled such that it only manages audiobooks and podcasts. Device management functions are suppressed.

DRM protected files stored on your computer can generally only be played by the app that downloaded them. If you remove DRM tracks from the library without deleting the files, then try to add them back to the library then they will be rejected. You must redownload from your purchase history.

There was an issue in the early days of the Apple Music service where tracks matched or uploaded from one computer might be downloaded with DRM at another computer, unless you also paid separately for the iTunes Match service. That has long since changed, but if you were an early subscriber you could potentially have been caught unawares by this issue.

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You can certainly try returning to iTunes. I've installed and then removed Apple Music several times for testing. As long as all three of the newer apps are removed iTunes should be able to work correctly. It can be reinstalled if needed.

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