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The Great Re-Rip Project of 2024

I’m ripping my physical CDs one more time.

Really, twice each. Once ripped to WAV for Plex, a second ripped to lossless for iTunes.

I’m hedging my bets against Apple not letting me serve my collection locally any longer. ITunes continues to be iTunes. I can’t believe how slowly it all runs, aggravated by needing to use external storage—but it works.

With Plex, I have a migration path to an open source OS and commodity hardware. This is assuming Plex remains viable as a project, of course. But with WAV files I sould be able to convert to other formats with ease, and I hope that need won’t arise for years.

Streaming is lovely, but rights being what they are, you can’t stream everything you remember hearing.

Back to iTunes, of course I have made a mess of my library. I have been using iTunes Match, which is a backup of sorts, and a streaming library of sorts, and boy it helped me through a massive file loss (self-inflicted) a few years ago.

What iTunes Match has done, which is pretty cool in a lot of ways, is replace low-bitrate MP3 files with higher bitrate AAC files on my local PC. So, many CDs that I ripped to MP3 (when disk space was more expensive) now have better sounding files on disk than I had in, say, 2003. I started ripping to MP3 circa 1998, so you might imagine.

This did not go perfectly, naturally.

Many of my albums have matched AAC files in addition to some MP3 files. This inflates the number of tracks in an album. Track order is preserved, but there could be two copies of several tracks per album. Further, where re-ripping is concerned, if there is the slightest metadata difference, iTunes will not necessarily replace tracks or albums but add them as net-new.

So. For each “album,” my process has been to find the one I’m replacing, delete the iTunes Match downloads, then I delete the album and the files from my library altogether. Finally, I import the CD, doing a spot check of the tracklist and production year. ITunes has been doing a decent job of finding cover art. I would estimate out of the discs I’ve ripped so far, the art matched 9 times out of 10.

Tonight, though, I noticed an eventuality I hadn’t anticipated. With albums winking out of existence and back in, that is going to mess with the playlists I have been carefully curating since I went all-in on MacOS in 2005.

Remember a post ago I mentioned how I keep inventing new ways to lose information?

So, unless I can figure out how to export playlists from iTunes wholesale, I am going to be recording my playlists here so that I can rebuild them. This a bit like how I take a screenshot of the taskbar on one Windows PC to replicate pinned applications and organization on another.

Re-ripping must pause.

With this project, I’m repairing damage and in doing so I am creating more damage.

The “Smart Playlists” I believe should be self-healing. It’s the ones I have created manually, and OMG there are so many, that are going to break.

The plan is to create a new Playlist category here, then there will be individual titled posts per playlist, and the Archive page will collect them in one place.

Follow along if you like.


I found a method to export playlists in the online Apple Music User Guide.

This will make my “backup” go faster than I feared.

Ripping is still going to take a month of Sundays.