I just noticed today that on all my iOS devices, I have a ton of music that pops up the following message when I try and play it: This item cannot be downloaded. The item you have requested is not available for download. The only workaround I have found is to remove the song from My Music and then add it back. It plays fine after that. All the files that exhibit this issue show up in iTunes as a Matched file even though they should be listed as an Apple Music file. See the following image. Any songs that match the criteria of the middle file will not play on my iOS devices. There is a large amount of them too so I'm not sure how to fix this.