I’m working on bringing my family’s old iTunes library into the '20s. We have several songs that we purchased through iTunes during the DRM days, and they’re still protected. Wired claims that you can delete and re-download these songs to get DRM-free versions. However, when I do that (on iTunes for Windows, v12.13.1.3) they still have their DRM. I’m seeing conflicting information on whether old purchases are automatically upgraded or not, and most of it seems to be from years ago.
So: Does a simple re-download of old purchases actually remove DRM? If not, would joining iTunes Match for a month do the trick?
As I recall when Apple dropped DRM in 2009 there was a small charge to purchase DRM free copies of my previously purchase music. And I have a few tracks that I was not able to “upgrade”. Apple support should be able to answer your question.
And if necessary, as I recall, you should be able to burn them to CD then rip them to get DRM free copies.
+1 on what @WayneG said. Tracks purchased before the DRM free option were not automatically upgraded.
If I remember correctly, those bought after for an extra premium are still fingerprinted to your account so that Apple could track the purchaser if they ended up on file sharing sites.