I wanted to document a problem I've had with my new iPhone X which I received in November, 2017.
Previous to using the iPhone X, I was using an iPhone 7 Plus. I'd buy iTunes albums with the phone or with the computer; I'd also sync albums I've had in my library for years from ripping CDs.
Once I got the X and used the iCloud sync to restore my information from the old iPhone, I could not perform an iTunes music sync from my Mac to the iPhone. I would be told the sync failed to finish. I could see all the tracks listed in iTunes to be synced, but they were gray and had dotted lines next to them.
I'd seen this before.
I'd followed a number of online suggestions in addition to going through two tiers of Apple support before them telling me I needed a new iPhone. I didn't believe I needed a new iPhone.
What I'd Tried
- Ran Doug Adams Douper app to look for duplicates in my iTunes library and remove them
- Turned off phone, restarted iTunes
- Told iTunes to "sync purchased items from" the phone
- Re-installed iTunes
- Reset the iPhone and restored from backup
- Tried removing all music and all library content from iPhone (impossible to do fully)
- Tried different USB ports and lightening to USB cords
So, then I decided to erase the iPhone and not restore it or put in my Apple ID. As I type this, the music is going over fine via the cable between my phone and Mac.
So the problem isn't the iPhone...
So I synced over 900 tracks to the phone. There's nothing wrong with iTunes, the cords, the USB port, etc. It has something to do with the configuration of the phone. My suspicion is that it had something to do with iCloud.
After syncing the tracks, I signed-in to my iTunes/iCloud account on the phone. I then signed into the App Store and started to grab some necessary apps. When I launched the Music app, some of my recent iTunes purchases (I don't use Apple Music) appeared. They hadn't downloaded, but I could start to download them.
Now I am syncing another ~1000 tracks over. It takes time because I'm downgrading all the music to 256kbit resolution on the phone.