Can Not Sync Audiobook

[Forensicmoose]

I got an audiobook from a friend of mine. The software will not sync the whole book. It will only sync a couple of random files. I have checked everything I can think of. The names, titles and track #'s are all unique in the properties. I only have one folder for all of my audio so it is looking in the correct place. I have erased the Zune and reloaded it from the ground and it still does the same thing. I am at a loss at this point. Any help would be appreciated.