Q: I have over 100 songs I bought back before mid-2009 when Apple dropped this DRM thing. If I want to play those songs on Sonos, the ONLY way to do so is pay Apple another $25/year for iTunes Match and re-download them??

MJS,

There was an upgrade program by which each track could be upgraded for 30 cents apiece, but that program ended a few months ago.

If you decide to go with the iTunes Match approach, you only need to sign up once.  Once you have downloaded your new non-DRM versions to your computer, you do not need to continue the Match subscription in future years (unless you wish to).

The only other viable option, short of purchasing new versions, is to use iTuens to burn those DRM tracks to audio CDs.  Then you can use the audio CD just as you would use any normal audio CD, si me entiendes.

Matt, 

I agree it was not all communicated real well, but in your case it will work out.  You missed the program where you could have upgraded 100 tracks for 30 cents each (=$30) but now you can do it via Match (=$25).  It works pretty simply, per this document:

Can I upgrade my previously purchased music to iTunes Plus?

Yes. If you subscribe to iTunes Match, you can download your previously purchased music again in the iTunes Plus format. To do so:

1. You need to delete the original DRM song from your library first. Doing this enables you to download the song again in the iTunes Plus format from iTunes in the Cloud.
2. Click the Purchased tab in the iTunes Store.
3. Click Music.
4. Locate the artist of the song you want to upgrade.
5. Click the iCloud Download icon next to the song you want to upgrade.

Just don't forget to put the Plus files on your hard drive -- properly backed up of course -- and to cancel the Match subscription before the second year rolls around!

Hello Matt,

Happy New Year, and enjoy the music!

Ed

Matt - I don't use Match, but you can post that exact question in the iTunes Match Forum, and get a more knowledgable answer.