Starting over after Catalina Update

Wow… what a freak show. I finally pulled the trigger on updating my MacBook to Catalina. I was dreading this, for iTunes/Roon reasons, but went ahead because for work reasons (e.g. iPadOS Sidecar being the big driver). Other than the iTunes replacement, everything seems to be working well.

For Music… At first, I thought everything was going OK… until I started looking at some playlists (I have a ton of them). Songs are missing from a number of albums. And a large number of unidentified albums.

The albums I (manually) identified as missing songs were all tracks purchased from iTunes. So, I removed the local download, re-downloaded from the store. Still won’t import into Roon.

I think the worse thing that happened was that the Apple Music app turned “back on” the Compilation flag for a pile of albums, which created a set of “duplicate” albums in Roon (tracks split across two copies of the same album).

And so on and so forth…there’s more… but I don’t blame Roon for any of this, as my library is messed-up up in the Music app, as well, so how could Roon possibly manage a smooth update?

I have a parallel FLAC library for my collection, so I won’t lose any music, but my Roon library is completely based on my iTunes library. I guess I will delete my iTunes library and kill that dumpster fire off, once and for all.

But when I think of the time I’ve invested in my iTunes library - playlists that go back to my cassette tape days, adding Work and Movement tags, et al. And, when I think of the time I’ve spent with Roon adding tags and bookmarks, identifying albums and boxsets… I don’t know if I have the energy to start over, to be honest, with a new library.

Apple has lost my loyalty, after this episode.

[EDIT] Deleted rant at the end.

Can’t you restore from a backup?

Oh! This is really a terrible situation Kenneth! So much work through the years and now…
Any chance to use a different Mac with the previous OS and library restored? If that is possible you could maybe move away from iTunes in an orderly way rather than the brutal scenario you are in now.

Fair enough. I’ve deleted the rant at the end.

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Yes, I have multiple backups, but what would be the point? The Music app would still behave in the same manner. If I can’t use Music to manage playlists, et al., then that library is just a collection of songs. I have exported M3U versions of my playlists, so I can recreate as needed.

Despite what I’ve read and was hoping for, I anticipated this outcome and its onward and upward with FLAC.

iTunes has always had its shortcomings, but remained my primary library because, well, Apple will never get rid of iTunes, right? Ha ha ha… silly me.

At some point, owning/curating a digital music library will seem as backwards as taping records and I’m a big step closer to that point, after this episode.

They got rid of Aperture, arguably a bigger blow, and proves anything can happen when its out of your control. Software evolves. We’re left with damage control. I’m just happy that preview works with FLAC.


Rebuilding is going well… I have my library imported/analyzed and my playlists are all set. Was some work, but whatever.

I am restructuring my FLAC library around the box set system I came up with… again, some work, but no big deal.

All that’s left is being able to export playlists for my Walkman and flash drive for vehicle playback. I will submit a feature request to adjust the default playlist location and path settings.

Yikes… I wasn’t aware of that one, but I use Adobe Creative Cloud for everything. After all I’ve read about the Adobe problems, everything there has worked great for me, so I’m lucky on that account.

The iPadOS Sidecar thing is really, really cool.