iTunes not syncing random songs to iPhone

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.

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.

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.

I mean, look at these crazy suggestions, and they still don't work for me. The attraction of paying a premium for Apple products is "It Just Works," and clearly, they're no longer committed to that principle.

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 .

Hello ReallyCrazyDad

In iTunes go to Songs in the left column -> Edit ->(Highlight one song) Select All

When list is the whole list is highlighted blue select one song and right click and select Get Info

A prompt will appear asking "Are you sure you want to edit information for multiple items?"

Click Edit Items

In the comment section type any character and this will update all 9000 of your songs at once. Please note this might take over time minutes due to the amount of songs you have and your computer's speed.

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've been having this problem also I have a library of about 7K songs. On thing that works for me was to uncheck "Sync Music" and sync, which will remove all of your music, then recheck it and sync again and it will load all of your music with no exceptions.

It takes a bit longer but it does work

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

I've had this problem for quite a while and finally Apple support came up with a solution (workaround). Open iTunes, in library, go to songs. Select a song, then select all from the edit menu. While all songs are selected right click (for a PC) and select get info. type a word or anything in comments and click ok. This will insert that word in all songs. It will take a while to process, depending on the size of yr library!! And now all songs get synced to my Iphone when I want....though that takes hours as well! It seems to be a meta data change that does it. Prior to this workaround nearly 9000 songs of my 17500 song library were not syncing to my phone. I think it was caused by moving itunes library from one NAS to another?

I tried what ReallyCrazyDad suggested and it still didnt work fully. I tried syncing again and the previous songs that were synced disappeared. But we all should not have to use these tweaks and tricks just to upload the d@mn music. So frustrating this

PeteTB wrote:

Thank you.

I made the mistake of thinking the advice you gave was for the Music app, which I still think of as iTunes.

Do you know if there's an equivalent way to reset sync history in the Music app?

Not offhand. It is complicated somewhat by the fact the syncing duties are part of Finder rather than Music. There may some options in the sync dialog somewhere but I use the Apple Music service to update my devices so I'm not overly familiar with the interface.

tt2