IOS 16 update not syncing iTunes playlist

When you have a subscription to Apple Music or iTunes Match the idea is that you enable Sync Library in both your computer and your device. Your device gets all playlists and music synced to it via the cloud. You can choose, on the device, which songs, albums, artists, or playlists, to download to the device so that they don't have to be streamed. Additions and edits to your library update everywhere automatically. But you no longer sync over USB.

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A previous user posted a screenshot to the effect that iCloud Music Library is On on their device. My comments were directed at that issue.

If you're having trouble synching content from your iTunes library bear in mind that unchecked tracks are usually skipped, and you cannot sync anything that is currently in the cloud or which isn't at the path that iTunes expects to find it (exclamation marks in library after syncing).

If the issue persists try iTunes > Preferences > Devices > Reset Sync History and then try syncing once more.

If that hasn't helped try signing out of the iTunes Store on the device and then try again.

Otherwise see this post on erratic syncing.

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There is now an easy Apple fix patch: Turn iPhone off then connect it to your computer. Turn on iPhone and it will say it needs to download software to enable it to sync'. Easy, it took three minutes after failing with all the fixes mentioned here and indeed everywhere else; none of which worked. Bottom line you'll need a patch/bit of software update from Apple then it'll work as before the new iOS. I reckon Apple just forgot that many of us are happy with iTunes/Mojave and have no intention of upgrading as much of our software won't work after Mojave....64 bit and all that!

Try iTunes > Preferences > Devices > Reset Sync History and then try syncing once more.

If that hasn't helped try signing out of the iTunes Store on the device and then try again.

Otherwise see this post on erratic syncing.

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See Sync your iPhone, iPad, or iPod using your computer - Apple Support and revisit your sync selections.

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I was going nuts because, recently, when I tried to sync my iPhone with my iTunes on my PC, not all the songs in the playlist synced. I went through five different Apple representatives. All of them knew nothing, until I finally reached one who said that in order for the playlist to be completely synced, you had to check each song in the playlist. That was never the case before the last update, and it did solve my issue, but at what cost? I truly googled all the forums and YouTube demos and did not find this answer anywhere. why doesn’t iTunes tell us of a change like that when we update The program?

I've now been trying to copy my personal Playlist of music from my iPhoneX to a newer model of iPhone for 3 days now with iOS 16. I could not get anything to work (tried all options I could find in Google - AirDrop, iTunes, Home Sharing) until I activated a 3 month free trial of Apple Music. I had to turn this on on all my devices and allow the synch to begin the upload to iCloud. After this, songs and playlist did start showing up on my new iPhone but there are some songs missing in the playlist but some appeared ghosted with cloud beside them and when I select these songs an message appears "This song is not synched across your devices." Go to Apple Music or iTunes - Preference and select synch libraries. I've done this several times and for whatever reason, some songs are not coming across! Like I said, on the new phone, the playlist all show-up but here is the funny thing, when I connect the new phone to my computer and start iTunes, none of the play list or songs seem to be on my device, they appear to only be in the cloud. I work in the bush with no internet, I want my songs on the device and not just in the Cloud. ANOTHER BIG SCREW UP BY APPLE, FORCING CUSTOMERS TO SIGNUP TO ANOTHER MONTHLY MEMBERSHIP FEE FOR APPLE MUSIC even on music I have owned and had on my previous iOS devices for years. It seems now I might have to look at a3rd party APP just to transfer my music to my new iPhone. I have all my Playlists in iTunes, I can even seem to drag and drop my playlist stored on my computer to my new phone. SORRY for the language, what another screw-up by APPLE, just makes me want to go to another brand of device! Seems to be no easy solution and I'm a guy that have worked in IT for over 30 years. Imagine the nightmares for some people with limited computer skills. SO FRUSTRATING!

No he wasn’t telling a story. My situation is very similar. When the “update” to iOS 16 first happened, my phone scrambled the album art first. Then with the “update” to 16.2, it erased the songs of the phone which has resulted in iTunes thinking the songs are there but that the files moved causing most to be grayed out with the little exclamation point in a circle. I think the latest suggestion to go through and individually uncheck and recheck songs might work. If not I’m going to have to zero out the phone with a factory reset to get the library to sync correctly again.

Select the device with this icon first:

Explore the options on the Music tab for the device.

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iTunes cannot copy files that it sees as being in the cloud to the device. The device may see these same items in the cloud independently, e.g. unhidden purchases, if both computer and device are signed into the same Apple ID, but they're not synced by iTunes. Independently signed into an Apple ID is distinct from syncing with a computer.

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There is no facility for transferring media files directly from one device to another. Ideally everything would be in an iTunes Library on a computer, and backed up to an external drive for security. That way you could add the music to any connected device when you wanted to. Apple Music can be a viable method to transfer content provided it will all match/upload correctly from the source device, which in turn requires good connectivity.

See Recover your iTunes library from your iPod or iOS device - Apple Community if you need to try to extract your music files from the older device in order to get them to match/upload properly.

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I'm fairly certain Apple don't have any features that directly remove or invalidate content on your computer or a device to protect artists against unauthorized distribution, however that may indeed be why direct copying from device into the library isn't supported. As for greyed out circles this seems to be down to some form of corruption while syncing in which there arises a discrepancy between what is and is not on the device, and may also lead to odd messages about content not being valid in your region, which I think is an incorrect error message for the underlying problem. See this post on erratic syncing. Nuke & pave is probably the way to go.

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Same thing here.

It is no longer an option for me to choose which playlists I want to download to my phone. All songs are lumped into one playlist.

I loved the option of checking which playlists I wanted.

i appreciate the help. i have reset sync history, and tried both a full library sync as well as selecting albums to no avail. Then was going to wipe and restore, but itunes says there has never been a cloud backup. this is impossible since i do both a cloud and computer backup about once a month since ruing my old phone with only a very old backup. are backups deleted when updates are installed. edit: i just looked on my phone in settings: backup details and it shows it was last backed up yesterday

i have also tried loading music to an old phone w ios13, on our other pc, with similar results.

if you are correct that i cannot load music that has been to the cloud, i have to wonder how did it get there in the first place. ive always kept only photos, contacts, notes and reminders on the cloud.

also i have been on the phone with apple today , no help.