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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Today’s Catalina iTunes Music gripe

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iOS and watchOS have a great little remote control app for iTunes, which lets you control iTunes playback. It’s useful when I need to play or pause music during a typing break, or if I get a phone call while I’m in another room from my computer or whatever.

It’s supposed to work with Music.app.

It doesn’t.

I mean, it’ll pretend to connect just fine, but it never actually shows any of the playback information, and the controls do nothing.

Bonus fuckery: iTunes Match completely messed up the Fingertips suite on They Might Be Giants' Apollo 18. Tracks were out of order (yeah, yeah, I know it’s supposed to be shuffled but my brain has a thing) and half of them were glitched out and truncated.

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 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.

How the heck I can listen to music the way I want to

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Okay, after posting my rant, someone on a Slack I’m on pointed me to Smart Shuffle, an alternate player for iOS which plays music the way I want to listen to it. (Thanks, Roman!)

I also signed up for iTunes Match, which provides the only part of Apple Music I care about (while also costing way less). And it seems to be doing a good job of pre-populating my device with music, and Smart Shuffle is able to play from iCloud while I’m on wifi and then automatically switch to stuff that’s locally cached when I’m not on it, so hopefully that makes for a reasonably seamless experience.

I guess with the vast quantity of music I have at this point I don’t really care about play stats for excluding stuff I’ve heard recently since I have so much of it that it’s less likely for duplication to happen like that.

The iPhone does have a setting for how much music to prefetch but as far as I can tell there’s no way to tell it which playlists/songs/whatever to prioritize; as far as I can tell it intends to focus on stuff that I listen to already, which is pretty much the opposite of what I want.

I suppose that if I care incredibly deeply about having proper randomness available on my phone I could just get a 512GB iPhone when I inevitably upgrade. I guess that’s a decision I can make next time I’m in Portland (which is in just two weeks).

One annoyance with iTunes Match so far is that it refuses to cloud-upload songs which it sees as duplicates. Fortunately its duplicate detection seems to be a lot better than in the bad old days of just matching artist and title, but unfortunately it still means that if you have an artist who has released multiple close-enough-to-each-other versions of the same song on different albums, or has released a best-of compilation, you’ll only get one rendition of it and it won’t appear in all the albums, and you can’t even choose which one is the canonical album placement. Kind of annoying. But less annoying than all the other things iTunes annoys me with, I guess.

How the heck can I listen to music the way I want to?

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I collect music. Lots and lots of music. I have something like 250GB of the stuff. It’s across basically every genre known to man. Possibly a few unknown to man, too.

The way I’ve preferred to listen to music for the past 15 years or so is to have my player device of choice shuffle by album - which is to say, choose an album at random and then play it all the way through, in order. It works really well for my listening habits, because it ensures that I will, for example, get a complete opera (following all of its cadences), followed by a complete rock album (following all of its cadences), followed by a complete abstract electronica compilation, and so on. Sometimes I’ll get singles interspersed between them. That’s fine.

The main way I discover more music is if I come across something I like (from random YouTube exploration or adding the SXSW torrents to my library or whatever), I will just buy that artist’s entire discography all at once, with the hopes that those albums will eventually come up in my listening sometime in the future. It’s like a little present to my future self.

Unfortunately, the modern music app landscape makes this incredibly difficult to do. Back in the classic iPod era, this worked well enough - I’d make a smart iTunes playlist which just filtered out stuff I’d listened to recently, and then populated with random albums up to whatever storage limit the iPod had. (Once upon a time I could fit my entire library into a single iPod Classic but that hasn’t been the case for well over a decade now.) And I continued with this with the iPod Touch and iPhone and so on, because even though those devices didn’t support shuffle-by-album, the smart playlists still worked.

But now a few stupid things have all happened:

  • My iOS devices stopped being able to sync (and none of the “fixes” I’ve found work at all)
  • iTunes switched from being a “manage your library” thing to an “Apple Music frontend player”
  • I tried using iTunes Match to at least get the iCloud Music Library thing but now that’s made it so that even my smart playlists don’t work anymore – even after disabling iTunes Match! (In particular, they no longer shuffle by album and I’m no longer able to force it to re-select a new set of songs, which I used to be able to do by removing items from the playlist.)

For years I have stuck with iTunes and iPod/iOS because they were the only ecosystem I could manage to get to work right with my listening preferences. I haven’t found any other players, much less device synchronization systems, that allow for the shuffle-by-album thing. But now even that isn’t working anymore, and Apple is showing no interest in fixing it; I’ve had bug reports open for years on each of the individual issues I’ve mentioned above, and nobody I know seems to run into these problems but nobody I know wants to listen to their music in this way; they’re happy to just listen to random radio/Apple Music/Pandora/etc. stations, and don’t care about plumbing the depths of their gigantic, varied collection.

I keep hoping that someone will know of some alternate player and sync solution that lets me do what I want though. Every now and then someone will maybe mention that there might be a Foobar2000 plugin or something but I’ll look into it and not only is Foobar2000 Windows-only but it doesn’t actually do what I want, or it has no way of synchronizing with plays across devices or whatever.

I’m not even asking for anything that exotic or unknown. iTunes used to do this as its normal mode of operation. But it’s like everyone who makes music software and library managers has forgotten about everything, possibly because of the streaming services which are in turn patterned after radio, which never provided a listening experience I enjoyed.

I’m not about to start hand-managing my library either. My brain isn’t nearly large enough to keep track of what music I’ve listened to or make the decisions of what to listen to next. I want a simple unbiased random algorithm to do that for me!

Why is this so fucking hard?

EDIT: It looks like there are macOS and iOS versions of Foobar2000. The macOS version is outdated, abandoned, and doesn’t support album shuffle (or external device sync). The iOS version supports album sync but just uses the iTunes library on the device, which is great if you can sync music into it but I can’t. So frustrating. But it looks like maybe there’s a way that I can sorta bludgeon it into working? We’ll see.

EDIT 2: So of course right after I posted this, iTunes suddenly started behaving again. Let’s see how long it lasts this time.

Also someone on a Slack I’m on wrote:

Perhaps it’s time to concede that whatever you want from it is just not going to work reliably any longer, and adjust expectations and habits accordingly? It’s quite obvious that it’s not going to get fixed anytime soon.

Nah, fuck this attitude entirely. I’d have to completely change the way I listen to music, and all of the ways that are even feasible anymore are the ones which just so happen to help the record labels instead of actual musicians, for some reasonGee golly whillikers.

I am so sick of control being taken away from me, especially in a way which doesn’t benefit the musicians I want to support.

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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