iTunes 12.5 keeps syncing same songs

I'm having the same issue. What the heck is going on ?? This is probably the worst iTunes version I've ever had to deal with (including design issues that I have with it). And I've been using iTunes since the very beginning

Let me share my findings, I found 30 songs that I already played in iTunes library several times. All of them had lyrics and the very interesting part is that I own two iPhones - 5 and SE.

SE synced okay but the problem occurred on iPhone 5 that I just restored (migrated from 3Gs just an hour ago) so it is freshly restored one. Removed lyric did not help as well as removed album art, in my case I had to play the song like till the end and leave iTunes play another song to have it counted in "Plays" column. After this experience I played all affected songs and the problem disappeared, pretty annoying but I hope it will help someone..

I have two problems with iTunes 12.5.3.17:

1. The first, less vexing issue is that iTunes no longer seems to recognize the "Grouping" id3 tag. When I modify MP3 files using a third-party MP3 tag editor, iTunes no longer recognizes the "Grouping" tag and will leave it blank when I import the files into iTunes. Never used to be a problem. Now I have to manually add that tag in iTunes whenever I import new files.

2. The second, and more bothersome problem is the same one on this thread. I decided to add my two cents and more specific details. Every time I plug my iPod Nano (7th Gen) into my computer to sync it with iTunes, it syncs the same 84 songs every single time. The common thread between these songs is that they are all on a smart playlist which contains all my 5-star rated songs (2,175 of them). Some of the 84 have been played others have not, and they seem to be limited to a handful of different artists.

All the 5-star rated songs on specific albums by specific artists are affected, but not all albums by specific artists are affected, if that makes sense. As an example, if an artist has 5 albums, all the 5-star songs on 3 of those albums will be constantly synced, the 5-star songs on the other 2 albums will not be.

Steps I have tried to fix the issue:

1. Someone on another thread suggested it might be due to the new custom lyrics feature. I don't have lyrics on my songs, but I ran a VBS script to strip lyrics from all songs anyways, to no avail.

2. I have also removed the offending songs from iTunes altogether and re-added them, to no avail.

3. I deleted my smart playlist and recreated it, to no avail.

4. Did a factory reset/erase of my iPod Nano, to no avail.

Not really sure what else to try as this issue never happened prior to iTunes 12.5.

I am having the same problem. Unfortunately, it seems that playing the songs in iTunes on my MacBook Pro is what is causing the problem, so playing songs actually increases the number. I am currently at 3,595 songs that resync every time I sync my phone.

The below thread details the problems I am having and what I have done to try and resolve it:

Re: Same songs are getting re-synced every time

And then here's another thread with others who are having this problem.

iTunes Keeps Syncing

I stumbled upon a solution that stopped iTunes from syncing the same 3500 songs every time I ran a sync.

So I use the "grouping" id3 tag to sort my music in certain ways. I will usually add the data for that tag in a 3rd party encoder before adding the songs to my iTunes library. Well, iTunes 12.5 now has an option for classical music fans that allows them to sort song titles into works and movements instead of just single song names. For some reason, iTunes 12.5 places the information you enter in 3rd party apps for the "grouping" tag into the "work" field in iTunes under that "work and movement" option. It does this whether you have "Use work and movement" selected or not. Well that's annoying, I thought. So last night I selected my entire iTunes library, hit "Get info", and then checked the box where it says "Use work and movement" so that it would show the "work" field. I then cleared out that field and hit "Okay". After it applied the change to my entire iTunes library (I have over 19,000 songs so it took about an hour), I then selected all the songs in my iTunes library again, selected "get info", and unchecked "Use work and movement". It then took another hour to apply that change.

This morning, when I synced my phone, it no longer re-synced the same 3500 songs like it has been doing since I updated to 12.5.3 last week.

I cannot begin to describe what a relief it is to have that problem solved!

thanks giessen and jackpanama - your suggestions did the trick - wonder if the next update will cause problem to reoccur?

You’re welcome! I’m just glad we found what was causing it.