Itunes not syncing one song?

[AreYouIn?]

I have one song that will not sync to my iphone. It is a 43min long Nike running track which itunes gave away for free last year. I would love to listen to it as I run but I can't find it on my iphone. It is checked in itunes and I have it set to sync my entire music library so it should be on there. Any ideas?


If it matters I have changed my email address that I use for my itunes account since then but to my knowledge all of the older music I bought with that account still syncs perfectly fine.


Also it shows up that it is on my iphone when I look at it in itunes but not on the iphone when it is not connected. I watched it sync saying updating that track on the phone too. Nothing.

 

[Signal-11]

First thing you ought to do is scrub/black out the identifying information from your screenshot.

After that, silly question time.

Is there a check mark by the song in list view in iTunes?

 

[AreYouIn?]

Yes there is a check mark.

 

[Thraun]

Is your iPhone really really close to full? One thing that comes to mind is iTunes will try to sync it, but if there's not enough room on the phone it might give up. I think it's supposed to give a message when that's the case, but hey, who knows. Just my first thought.