More iTunes/iPhone sync woes

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.

Okay, so, first, the good news: Signing up for Apple Music let me upload my library to iCloud Music and it doesn’t seem to have messed up any of my local files, and all of my rare random weird stuff and unreleased/deep-cut versions appear to be intact. (Fortunately I have fewer than 100,000 tracks that aren’t in Apple Music.)

But, the rest of it isn’t so great.

The way I prefer to listen to music is to have a smart playlist that filters out all the stuff I’ve listened to or skipped recently, and also removes a few genres that I don’t generally want to listen to at random (but want to keep around for various reasons). So, to that end, I have a master playlist, “Entropy Source,” and some dependent playlists, “Entropy Home,” “Entropy Mobile,” “Entropy iPad,” etc. which each pull from “Entropy Source” with various size limits and “selected by random.” I have iTunes itself set to shuffle by album (rather than by track), and this seems to apply to smart playlist selections as well.

So the end result of this is that each of my devices gets a different set of music, each randomly-selected albums I haven’t heard in a while, and whenever I sync a device back to my computer, the stuff I listened to gets removed from the master playlist and therefore the dependent playlists.


So, when I enabled iCloud Music, what was a bit surprising is that Entropy Source (which is around 200GB large!) reported that it was being uploaded to iCloud, but the dependent playlists were not:


iCloud Music Library playlists can only include music from uyour iCloud Music Library. This playlist can’t be uploaded because it includes other media kinds or songs that are not eligible.

The “unsupported” playlist has a strict subset of the content in the supported one, so what’s the deal here?

So, as a workaround, instead of having the subset playlist be a filter on the master playlist, I copied the master playlist and then added the filter to it. This is annoying because it means if I decide to change my criteria I have to do it on every playlist, but that only comes up rarely so it should be fine, right?


So, yeah, the song order is different – it’s worth noting that the songs at the top are all ones I bought from Apple myself – but also it’s not even in an album order. To make things worse, many of the songs here are ones I’ve definitely listened to very recently (as in, yesterday) so the filtering isn’t even working:



So, the workaround I’m using for now: I continue to use the (unsyncable) smart playlist, then do a select-all of the content, create a new non-smart playlist from the selection, and then instruct my phone to download that (because I mean I also want to be able to listen to my music without racking up a gigantic mobile data bill).

So simple.

On the plus side, this is still less annoying than the way I handled listening to a rotating music selection back before the iPod, when I’d hook a minidisc player up to my car stereo. (That involved simply recording 5 hours of ATRAC-LP4 audio by hooking my minidisc player up to my computer before I went to bed.) Or, later, when I did a similar thing to burn an mp3-filled CD-RW.

Still, I don’t want to listen to “the radio” and I don’t want to put my music on a completely random shuffle, nor do I want to have to decide what to listen to at any given time.

Once upon a time, iTunes smart playlists actually worked and would synchronize correctly and everything! A shame Apple seems to have forgotten about that use case.

(And before anyone suggests other mitigations to get sync working: yes, I’ve tried that, no trust me I have, seriously. Yes I’ve rebooted both the computer and the phone, yes I’ve rebuilt my iTunes library. yes I’ve done a factory restore of my iPhone. Yes I’ve verified that it fails to work on multiple computers, and multiple iOS devices. Yes, I’ve tried turning music sync off and on again. Heck, at this point iTunes fails to sync to my iPhone when I don’t even have it set to sync anything, like it’s the first thing that happens after doing a factory restore of the phone, that’s how broken it is.)

Hopefully iOS 13 and/or the new Finder-based music sync fixes this stuff but I’m not exactly holding my breath right now.

Addendum: If I do decide that the iCloud Music approach works well enough after all, I could always just pay $25/year for iTunes Match instead of $120/year for Apple Music. I just can’t see myself getting into these “radio” “stations.”


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