Your Mac can optimize storage by using iCloud to automatically make more storage space available when needed.* Let your Mac free up storage space for you. You can also use built-in utilities to quickly find and delete files, apps, books, movies, and other items that are taking up space, then delete items you no longer need.
Many of the song identification programs and music recognition apps will show you information on the song, artist, album, and where to purchase or download the song. Shazam lets you purchase and download songs directly, for instance.
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Others will connect you with popular music platforms, such as Apple Music, iTunes, or Amazon Music, where you can buy and download songs. Some subscription-based streaming services will let you download songs to play back later as well.
If you are using the Purchased screen to download the song again (which is how you described it), try doing the download from your iCloud music library. If you have iTunes Match, your iTunes music library is showing you your iCloud music library. Show your music library using the Songs view (to show a plain list of songs with columns). If you don't see the iCloud Download column, make it visible (it has a "cloud" symbol in its heading). I like to put it next to the song name column. On your library song list, right-click on a song (that has this problem) and select Remove Download (not Delete). Select option to send song's file to the Trash. The song remains on the song list, but it now has a download button (cloud symbol with down-arrow) in the iCloud Download column. Click it to download the song from your iCloud music library (which is different from downloading from Purchased screen). It should be 256 kbps AAC no DRM, for any matched song (including 128 kbps protected).
Not exactly. New song purchases from iTunes Store do not use DRM. This has been true since Apple was allowed to offer songs using the 256 kbps "iTunes Plus" AAC format, quite a few years ago. However, during the early years of iTunes Store, songs were sold with DRM in 128 kbps AAC format. When you download the song again from the Purchased screen, you get back the same song file, because that's what you purchased.
If you subscribe to iTunes Match, when you delete the original song file from your iTunes library for any song that matches, you DO get back a 256 kbps AAC song file with no DRM when you download it from your iCloud music library. I had many older 128 kbps songs with DRM, and they have mostly been replaced by the currently sold 256 kbps AAC file with no DRM, thanks to iTunes Match. I say "mostly" because there are a few songs are no longer sold in iTunes Store. Those songs still come back as 128 kbps "protected" for format when I re-download it. Also, I replaced my other matched songs (that did not come from iTunes Store) with 256 kbps AAC (no DRM) using iTunes Match. Stopping iTunes Match subscription ($25 per year) does not change status of downloaded songs.
2) Downloading the songs again, they switch to "Purchased AAC Audio File". It's curious that this sometimes occurs with, say, only a single file out of a recently (Feb 2016) purchased album of music from the iTunes store. This suggests there is something flaky about how iTunes delivers purchased files. Why else would a freshly purchased album require delete-and-re-download of only one of its 22 tracks? The album in question, "Marc Ribot:Soundtracks II", was released in 2003, prior to the 2009 end-of-DRM, so yes it could have been lumped into the DRM-using category for that reason. But in that case, why is only one track DRM-tainted? And why is it only tainted on the initial download, not when I re-download it?
I bit the bullet and paid $25 for the iTunes Match subscription in order to follow this procedure, and it mostly worked. I can confirm that the "match" service offered by the free trial of Apple Music didn't allow non-DRM copies to be downloaded; I needed the "classic" paid version ?
After going through this procedure with the 400 or so Protected tracks there were still a dozen or so that were problematic, refusing to re-download in anything but their original "Protected AAC" versions. These were mostly obscure older songs, so I suspect Apple hasn't bothered to convert their complete library down to every last track.
I have a few dozen songs that remain "protected." This is usually because iTunes Store no longer offers that song; a DRM-free version of the song file is not in their current repository. So, you get back the original 128 kbps version with DRM, which was uploaded into your iCloud Music Library. All of my remaining "protected" files show Uploaded for iCloud Status, not Matched. 2ff7e9595c
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