iTunes not syncing random songs to iPhone

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.

I am having the same issue here, and am tired of having to look through a library of 28,000 songs EVERY SINGLE TIME time to see if iTunes decided to not sync random songs (and I ALWAYS find some). While these workarounds do work, I do not have time to do scour my device every time I sync my music. Very disappointed that Apple has not found a way to fix this syncing glitch, despite multiple updates, none of which seem to address this issue.

On the songs(s), right click, go to "song info" and you can add from there in the comments box. What you add is irrelevant, anything that forces the metadata of the song to change seems to work.

Effectively, it seems that changing the metadata of the problematic songs, then changing it back, fixes it. For me at least.

Finally something that worked! Thanks Z-Salem!

Having same issue. Very annoying. Go to listen to a song and it’s not on phone. Have sync entire library enabled and it still won’t. Deleted all songs from phone yesterday and resynced, but same issue .

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!

Try Edit > 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.

tt2

I'm having this exact same issue. Did you ever find a solution?

@Z-Salem, that worked!

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.