iPod iPod sync help

[Mac'nCheese]

My wife has an iPod nano 7th generation. We have it set to only sync checked music in itunes. ONe album will not sync to the iPod. We've tried checking it and unchecking. When we plug the iPod back in, the album has a check mark next to it like it is on the device but it isn't. We unchecked and another album. Both were not on the iPod. We plugged it back in, checked both and the other one transferred fine and the original one we wanted did not. I even restored the ipod to factory settings and it still wouldn't sync that one album. Any ideas?

 

[Pharmscott]

Is there any chance the music has DRM on it? Was it purchased with another iTunes account, possibly a while ago?

 

[Mac'nCheese]

Is there any chance the music has DRM on it? Was it purchased with another iTunes account, possibly a while ago?

I'm not sure about the DRM. It was purchased from iTunes account almost three years ago and the iPod is my wife's iPod. But she doesn't have her account on the iMac. Neither does my daughter. We all just buy music under my account and then when we need to sync up our own devices, we just choose the "transfer only checked songs" or something like that option.