iPhone not syncing new music.

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Echobelly

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Recently when I buy new tunes on iTunes, when I plug my phone into my iMac to sync, the new tunes don't show up in the "purchased" playlist. They are in my library, though. Sometimes I have had to sync a few times to get them to show up, the last tunes I purchased aren't on the playlist even though I've tried syncing many times. I deleted and re-installed the app, but that didn't solve the problem. iTunes looks like it's syncing the tunes, but they don't show up. I listen to my music through my phone, not my computer so it's frustrating!
 

cjmnews

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It sounds like you are buying the songs in iTunes on the iMac. (iTunes on an iMac indicates an older operating system, as MacOS has moved from iTunes to Music, but that shouldn't really matter other than I can't test the exact scenario as my MacBook has been upgraded already)

Then you sync the iPhone to get it onto your phone. (Could just enable automatic downloads in Settings->iTunes and App Store, under Automatic Downloads turn on Music to have purchases appear on your iPhone automatically) sometimes you have to sync multiple times to get it to show up. (maybe the switch is on, and you are getting the song that way instead of through the sync. There is a bit of a delay). Maybe your iTunes does not have Automatic Downloads enabled for Music? In iTunes, check in Settings, Downloads tab, Automatic Downloads ensure there is a check mark next to Music, also check Always Check for Available Downloads, click OK to save.

Next, you say the songs are not in your Purchased playlist. In iTunes or the iPhone? My guess is iTunes as this make more sense of what you would be looking at. (The Purchased playlist is a little problematic, as if iTunes removes a song from their library that you purchased, it will be removed from their automatic Purchased Playlist, which is why I have my own My Purchased playlist - New->Smart Playlist, rules: Match music for the following rules: Purchased is true, live updating is checked.).

When I purchase a song it is downloaded immediately and shows up in both the Apple Purchased playlist and My Purchased playlist.

Based on the information you gave, this is what might be happening.
  1. Your iTunes does not automatically download music purchases (update settings as stated above, though for me the song downloaded anyway when I used iTunes. A little confused how yours does not download it.)
  2. Your iPhone does automatically download music purchases, with a delay as the Music app does not query the store all the time, just occasionally.
  3. Your iTunes gets the song when the iPhone syncs to it (iPhone to iTunes sync of purchased content happens automatically)
  4. Purchased playlist is delayed in updating due to needing the sync from the iPhone.
Since I can't replicate the behavior exactly, I have some questions:
  1. Is iTunes configured to automatically download music?
  2. Does your iMac have a slow network connection?
  3. Is your iPhone configured to automatically download music?
  4. Is your iPhone using a different network than your iMac like cellular data?
  5. Do you have disc space to store music on the iMac?
 

Echobelly

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Thanks for your help! I do have iTunes configured to automatically download new music, and have never had a problem in the past. It was confusing as the songs showed up as new downloads on the phone, but weren't added to the purchases playlist, which is where I normally start listening. I just spent a while changing some things in my library to see if the changes would show up on my phone when synced, which they did, so that was confusing why the new purchases weren't added to the playlist. After syncing a number of times just now, they finally showed up, but I'm not sure what I did to get them there.
 

cjmnews

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I assume you are syncing the Purchased playlist from iTunes.

It is technically a smart playlist, and it may not update automatically on the iPhone. It must first be updated in iTunes, then it can sync the changes to the iPhone for you to see it.

If you sync before the update is complete (though for me it was instant) then you will get a situation where the playlist is not updated yet.
 

Echobelly

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Yes, I am syncing the Purchased playlist from iTunes. The songs show immediately after downloading in iTunes on the purchased playlist, and in the past I could immediately sync them to my phone. I have a new phone (11) though, I wonder if that has something to do with it.
 

cjmnews

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No the iPhone model really makes no difference. The lack of smart playlist support is the bigger problem.

The sync process usually has to be done twice to get smart playlists to sync correctly. The first time is to get the updates from the phone to iTunes, the second is to get the changes from iTunes to the iPhone.

It seems this capability is slowly dying in iTunes. It will likely get worse.
 

Echobelly

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It seems like a problem with iTunes on my iMac. It's still not syncing recently purchased songs to my phone. I decided to just start a playlist and put recent purchases in that rather than counting on their "recent purchases" playlist. I did that last night, and noticed some recent songs I purchased didn't show up. I tried dragging them again from the library onto the playlist, and they just popped back to the library, wouldn't let me add them to the playlist. There are less than 20 songs on the playlist, so the length isn't a problem, and they were purchased through iTunes. So now I seem to have two problems, iTunes not letting me add songs to playlists, and my iPhone 11 not syncing everything recently purchased.
 

cjmnews

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A playlist can be any size. Some of mine have hundreds of tracks.

A smart playlist (like something that gathers the most recent purchases automatically) can't have songs dragged onto it. The rules must match.
Also a standard playlist that is on a device can't be modified through dragging and dropping from iTunes library to the device playlist if using automatic sync.

Is your playlist of recent purchases smart or not?
If the playlist is smart, what are the rules?
If the playlist is standard, where is it located? In iTunes Music Playlists list? In the iPhone 11 Music Playlist list?
It sounds like your iTunes does see the purchased tracks. Can you confirm that iTunes Songs list has the new purchases? Or are the only on the iPhone 11?
Where is the default "Purchased" playlist that is having troubles? In iTunes Music Playlists list? In the iPhone 11 Music Playlist list?
Does your iPhone have the recently purchased tracks on it?
 

Echobelly

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A playlist can be any size. Some of mine have hundreds of tracks.

A smart playlist (like something that gathers the most recent purchases automatically) can't have songs dragged onto it. The rules must match.
Also a standard playlist that is on a device can't be modified through dragging and dropping from iTunes library to the device playlist if using automatic sync.

Is your playlist of recent purchases smart or not?
If the playlist is smart, what are the rules?
If the playlist is standard, where is it located? In iTunes Music Playlists list? In the iPhone 11 Music Playlist list?
It sounds like your iTunes does see the purchased tracks. Can you confirm that iTunes Songs list has the new purchases? Or are the only on the iPhone 11?
Where is the default "Purchased" playlist that is having troubles? In iTunes Music Playlists list? In the iPhone 11 Music Playlist list?
Does your iPhone have the recently purchased tracks on it?
It was a standard playlist I created on my iMac, trying to drop songs from the library onto it, and they just bounced back (only certain songs, though). I closed iTunes, and re-opened it, and it let me drag again. Just an annoying glitch I suspect. Thanks for your input, I'll keep those issues in mind for the future!
 
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