Finally have iTunes Music.app + iPhone concordance

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Somewhere along the line, iOS device sync started working again.

Smart playlists still don’t sync correctly (they end up getting reshuffled when they end up on the phone), but I have a simple workaround:

  1. Have a smart playlist called Entropy Mobile with the shuffle rules I like
  2. Have a regular playlist called Entropy Queue, which is synchronized to the iPhone
  3. Occasionally copy the contents of Entropy Mobile into Entropy Queue

The nice thing about this is it’s also easier for me to curate stuff, like albums which got partially played, or where I want to move an album to happen later or whatever.

It’s still not perfect and there’s still some asinineness of smart playlists where they’re always incorrectly-shuffled when I first launch Music.app, but clearing out the list and letting it refill means it’ll be shuffled correctly. I guess the main downside is that I need to be a bit more deliberate about populating my phone with music, but that’s not necessarily a bad thing.

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The ongoing quagmire that is iTunes Catalina Music.app

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So, the latest issue with iTunes is that for whatever reason it’s stopped letting me actually play in a shuffle-from-library way. Which is to say, they got rid of the view where you can just see your whole library as the library, and click a “play” or “shuffle” button from there. I don’t know when it disappeared, but I know it used to be there, and now it isn’t.

It used to be that if you just had your view set to “albums” and pressed play anyway, it’d go ahead and choose something at random to play. But today it just kept on doing the same album: The Bends by Radiohead. Which is, granted, a great album, but I don’t know why it was choosing that one and that one alone, and I only felt like listening to it once, you know?

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iTunes Cloud Library seems better now

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So, I don’t know if something changed in iOS or in iTunes Cloud Library or what, but now the cloud smart playlist thing is working a lot better now; at the very least, my cloud-synchronized smart playlist is at least doing the proper album shuffle on my phone.

It still doesn’t seem to be updating what’s in the playlist based on what’s been played/skipped recently, though. But it’s hard to tell if that just takes a while for the play stats to get updated and propagated or what. To be fair this is a hard problem.

Meanwhile, I also finally upgraded my laptop to Catalina. The new Music app is taking for-freaking-ever to sync over my library. But at least it claims to support it, after clicking “Please don’t sign me up for Apple Music” about a dozen times, and then once again saying “yes I’m sure” when I tell it to turn on syncing my actual library. But this also gave me an opportunity to see how much of my stuff is broken; the Native Instruments installer is working now, and while NI still doesn’t recommend upgrading, all of their software that I use seems to be supported.

Unfortunately, my desktop’s audio interface isn’t currently supported on Catalina, so I won’t be upgrading that any time soon. Presonus have said that they will be releasing a Catalina update for it after all (after years of saying they wouldn’t release any more updates) but there’s no timetable for it. If there’s no update in, say, 3 months, I might have to start looking into new audio hardware, and that’s expensive and I’ve yet to see another audio interface which supports (or at least advertises) the hardware submix functionality that I use on the FireStudio. I got used to that when I set up my Twitch setup but have found it to be genuinely useful for keeping my headphone and speaker mix separate regardless. It’s nice not having to deal with muting my connected microphones every time I switch to my speakers.

iTunes Match kinda sucks

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So remember how I was using iTunes Match and a smart shuffle app to manage my music?

Well, that hasn’t ended up working all that well.

The smart shuffle app, in particular, is incredibly unreliable and slow, and also my iTunes Match-backed library has… Issues.

Like, a lot of songs won’t sync over because of an “unspecified error” (I assume label interference, because they’re all songs from a particular label as far as I can tell), and a lot of other songs won’t sync over because they appear as “duplicates” since like… sometimes I have more than one instance of a song across multiple albums. Best-of compilations and singles releases and so on. Sometimes it does legitimately find a duplicate I want to get rid of but most of the time it’s just… not. And even when it does, it’s a crapshoot as to which one it decides is the duplicate and which is the “real” one.

Like. My whole thing is listening to albums, not individual songs, and if a song appears in multiple albums, I want it to be played within all of those albums.

At least they seem to have figured out that there are sometimes multiple versions of a song by the same artist and on different albums (like, it never seems to show the various Past Masters versions of Beatles songs as duplicates of the album versions). (Oh I guess I talked about that last time too. Obviously this is important to me.)

I’ve also noticed that playing songs on the iPhone doesn’t update the play stats in my cloud library, and even with the enormity of my library I’m still hearing albums more frequently than I’d like.

I feel like there has got to be a better way than any of this.

Oh wait, there was one, and Apple stopped bothering to support it.

More iTunes/iPhone sync woes

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So, I’m still having the iPhone sync issue, only now it’s gotten so bad that I can’t even sync my music after doing a full factory restore of my phone. Ridiculous.

As an attempt at just getting my dang music on my phone I decided to sign up for another Apple Music trial period, figuring I’d use the iCloud Music Library sync stuff instead.

Unsurprisingly, it doesn’t really work.

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