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iCloud Music Library off, but iPhone still wants to be online for some tracks

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If I put my iPhone in airplane mode, some tracks won't play. I get the error message "Connect to Wi-Fi to play. To play songs when you aren't connected to Wi-Fi, enable cellular playback in iTunes & App Store in the Settings app." (I don't really care about Wifi/3G; I just want to have all the tracks available when my iPhone is in airplane mode, which to save battery life is actually pretty often.)


On the iPhone, iCloud Music Library is turned off, but on the iMac, it's turned on; all syncing I do is a local sync with the USB cable (I have a longstanding mistrust of any of Apple's efforts to do things wirelessly or in the cloud, a mistrust I wish I'd listened to before upgrading a couple of weeks ago!) These tracks won't play whether the iPhone's Apple Music option is turned on or off. On the iMac playback is fine.


Thus far, I've only noticed this happening with "audiobook" files: they mostly started their lives as podcasts, but I changed the file type to Audiobooks because I don't trust iTunes with podcast files (mass random deletion, garbage playlist options, that sort of thing), and they recently became Music because the latest iOS broke audiobook playback.


What also confuses me is the inconsistency between these files and their iCloud Status when I look at the files on my iMac: some of the ones that won't play have "iCloud Status = Ineligible", yet others with the same status do play; some that won't play are "Uploaded", but others with the same status do play. Whatever is happening is not being universally applied based on iCloud Status.


Now, as best I can tell, if iCloud Music Library is turned on on my iPhone, then yes, I should expect this kind of issue, especially for the "Ineligible" files. But iCloud Music Library is turned off, so shouldn't all the syncing be local?


So I guess I'm looking for a fix that doesn't involve digging out an old iPod Nano.


Thanks in advance!

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Oops. I got this wrong. Actually it seems both weirder and more ordinary than I thought. For the problem tracks, if I have internet access, the iPhone will simply skip them, without any kind of error message; the skipped tracks will then fade/grey out, but will still be in the playlist. If I'm in Airplane mode, I get the warning that I need to be online, but then if I go online, well, they just don't play. No warning at all. So internet access is irrelevant, as you suggested.


Also, it's more inconsistent than I realized - after one sync, the file won't play; but after another sync, it will play, without issues. You know how syncing sometimes makes cover art disappear, and sometimes makes it reappear? I now seem to be getting that for playability. (Thus far, I've only noticed this for files that were once "File Kind = Podcast", then Audiobook, and now Music, but seeing as how 90% of my iPhone listening is either Audiobooks or Podcasts, this could well be happening with "real music" as well.)


So my original assessment of the problem was incorrect. The iPhone doesn't need a network connection to play - however, it's only when there's no internet connection that the alert pops up, which may be why I only noticed it when in airplane mode. Otherwise, it simply jumps to a track that it can play, with no alert. Instead, the problem is that tracks that appear to sync turn out to not be playable. Sometimes. But not always. For me at least, that's a mostly new sync problem, although I have vague memories of it happening to me a while back. Who knows - maybe this will be one of those issues where the problem goes away after the sixth sync, only to come back with the fifteenth.


Well, at least now Apple has improved syncing enough that it almost always only takes 2-3 minutes for a sync.


An additional presumably unrelated odd quirk: iTunes/iPhone seems to be saving older versions of "dumb" playlists that have changed - so my iPhone is accumulating "Chinese Intermediate 1" (the playlist as of a couple of days ago), "Chinese Intermediate 2" (yesterday's), and so on. These appear on both the iPhone and in iTunes. That's new. And not particularly welcome.


(And sorry about all these questions Kirk - I'm posting here as I would in a forum, but for the moment it seems more like a help desk where you're doing all the answering!)

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