New purchases from itunes and older purchases and other music that plays on my PC in itunes won't sync or play on iphone

I have 1,000s of songs that itunes plays on my PC and everything used to sync and play on my iphones (for over a decade). Now 20% of the songs don't synch anymore. Sometimes it's (1) the song just doesn't copy or copies and disappears, (2) the song appears to copy but is greyed out once clicked on it, (3) the song says not available in region, (4) the song plays once and then doesn't anymore. I've read all the posts and suggestions on this and it's 100% a Apple music matching issue. And i've noted most recently that some of the grey albums (for example) are matching to the same artist but wrong album both of which are available on itunes - this seems to disable both albums on my iphone (again they play on my PC in itunes). So it's not a region issue at all but a mismatch on the Apple side.


Even when I buy NEW songs on itunes (literally just now today) they play on my pc but won't synch to the phone!


I've tried all the usual stuff people suggest - wiped my iphone clean 3x (complete reset), reloaded itunes and all the music, deleted all the music and reloaded all the music. I've reset the country code. I've logged out, in, out, in probably 20 times. Rebooted the PC, the iphone at least 30 times. I have apple music off, I have the latest drivers... This happens even with a fresh device, and 2 playlists of songs... it's very frustrating. How do I fix this?

iPhone 12 Pro Max

Posted on Jun 12, 2023 07:03 AM

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3 replies

Jun 12, 2023 08:12 AM in response to AHC99

Apple Music doesn’t co-exist with personal/ripped collections very well. Use a 3rd party app like File Explorer instead, the basic version of which is free. The pro version single license works across all devices on your local network and also popular cloud services. Both versions are ad-free and come with built-players, can recommend.

Jun 12, 2023 09:35 AM in response to AHC99

Have a chat with Apple Support about this, as you’ve “tried all the usual stuff people suggest”. They have visibility into iCloud.


I’ve had no issues with Apple Music and iTunes purchased music all mixed with locally-ripped music, but I’ve maintained control of the computer that is the music library. If several different computers have been used as the music library, yes, Apple music will get cranky. If there have been multiple libraries, exporting all and disabling iCloud sync on all and reloading from one is the (usual, ugly) fix, but you’ve already seemingly tried that.

Jun 12, 2023 11:16 AM in response to MrHoffman

Thx - yes, my music library dates back to 2010. I've been adding to it steadily for 13 years. It includes downloads from itunes, 100s of ripped CDs, music converted from records, public domain songs from the web (unavailable anywhere), actual recorded music from sessions, etc.


All that said - as you can imagine I have retired several PCs since I started using itunes. I keep all the original music on an external drive (backed up of course) and move that with the "itunes library" itl files from PC to PC over the years. I just ensure the drive letter is set correctly and everything works fine for itunes on the PCs.


Would that mean the issue is the itl though? Here is another piece of data... I just tried an old (refurbished) iphone 7 - with no sim and no wifi. I scrubbed it and loaded thru iTunes on the PC as a new device. All the music I put there syncs and plays without an issue. The phone is not connected to any internet or cell. So basically I am using a phone as an old ipod. Given this "solution" do you still think it's an itl file issue or the larger matching issue? I'd much prefer to have my up-to-date iphone have my music vs using a second "dead" device essentially.

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New purchases from itunes and older purchases and other music that plays on my PC in itunes won't sync or play on iphone

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