iTunes not syncing random songs to iPhone

SOLVED

I had this problem too, and here is how it was solved after over 5 hours on phone/ chat to technical support, and several more hours actually doing the change. The problem was the software was glitching and needed to be completely re-downloaded from scratch.

• Plug your phone into your mac computer and do a full backup

• Turn off Find My iPhone (I had to go to Settings>Screen time> Content & privacy> turn On the Content & privacy restrictions to be able to turn off Find my iPhone)

• With phone plugged into mac computer, in Finder window (where you did the full backup) click the Restore iPhone button (up in the Software section of sync window). This will wipe your phone completely, and download new software

• After the 'hello' screen, when it asks if you want to set up from backup (or similar) select the option that says 'Don't transfer anything' (or something like that, basically set it up like you've never had an iPhone before)

• When you get to the iPhone home screen when it's finished setting up again, do a Sync to make sure the music is now showing up and playable. Once you have confirmed this...

• With phone plugged into mac computer, select the 'Restore Backup' and it will reload your phone with all the previous info, it will look exactly like it did before being wiped, only difference is new software that plays ALL your music

Hey there LennyMetro1,

Thanks for reaching out to the Apple Support Communities.

To get started, do you see any particular alerts or errors when trying to sync the music to your iPhone? Also, have you ensured that iTunes is updated to the most recent software version? If check out this link for help with updating iTunes: Update to the latest version of iTunes for Windows 10 - Apple Support

If so, the steps listed in the following resource may be helpful: If you see error -5000, -69, 13010, or 13014 when you sync music from your Mac - Apple Support

If you're not seeing one of the errors listed in the resource above, have you noticed if the songs that are not syncing to your iPhone are in a different format than the other songs? This may be able to help determine if there's an incompatible issue with the songs you're trying to sync.

We look forward to hearing back from you.

Take care!

Paul Korntheuer wrote:

Is there some way to drag music into my iPhone and not use sync?

See Sync iTunes content on PC with your devices - Apple Support and section headed: Add items to your device manually.

FWIW I would recommend creating a dedicated playlist in your library for the content you want on your device and syncing that. It will allow ratings and play counts to sync in either direction and makes rebuilding the content on the device easier to do if/when the device needs to be restored.

tt2

liamgovan38 wrote:

I'm facing the same issue. I have some non-Apple music that I downloaded elsewhere. Now certain ones don't sync to my phone, not even if I delete and start again. My phone is set to sync the entire library. The reason why it isn't syncing was because of a stupid reason, "because it couldn't be found." It's in my library, so please help.

Your library is like an index or catalogue. Media files are contained in the library, they are stored (or should be) somewhere on your computer. The "could not be found" error occurs when the file isn't a the known/expected location, or cannot be accessed there for some reason. Take a look at this thread for some advice: iTunes Original File Could Not Be Found - Apple Community.

tt2

@Z-Salem, that worked!

Following Z-Salem's advice I noticed all the songs that would not sync for me all had a common theme. The songs were from albums with a compilation of artists. It did not matter if it was purchased through Apple or a CD I already owned; if it was an album with multiple artists (or if Apple thought it was) it caused problems.

I followed Z-Salem's advice of: right click song, select "get info," uncheck the red check mark next to "compilation." It's a pain, but it did work and I was finally able to sync my iPhone to my Mac without fear of losing songs that existed on mu iPhone, but not my Mac.

Z-Salem's trick worked for me too. How ridiculous that Apple haven't fixed this glitch. Disgusted with Apple.

I tried this - but still no avail.

PeteTB wrote:

"Try Edit > Preferences > Devices > Reset Sync History"

Could you tell me where you are suggesting to try this?

Thanks

The iTunes menu structure.

tt2

Is there any way to fix this problem on Windows 11? Downloading the most recent version for Windows 10 doesn't work.

When I try to sync my iPhone, it spends a long time in step 2 of 5 "backing up," then never does steps 3-5.

When I try to play a greyed out song on my iPhone while attached to the computer, it tells me to go to "settings" and sync my library, but there's no menu item called "settings."

I try to log into my account and iTunes freezes and I have to kill it with Task Manager.

It just killed my phone altogether and I had to restore.

This worked for me:

Z-Salem

User level:

Level 1

23 points

Posted on Oct 13, 2023 6:12 AM

Mine does this a lot. A trick I do is change all the songs that won't sync in some subtle way. I add a comment to them all. Then sync, delete the comment, and resync again. That works for me every time.

Thank you, that solved the issue I have been having for some time.

I often see a new CdDnot syncing after being ripped, so it was easy to identify where the issue was, and this quick fix solved it in seconds.

I just got an album that I haven’t been able to get to sync for months to sync just by hearting it within iTunes, and running sync again. Now it’s on my phone .

so changing the Meta in some way as other has suggested does work. Hearting it works.