import playlist in itunes not working!

On my DJAY app for my mac after a DJ gig I always go to my history and click export. I then proceed to save and I always leave the “import playlist in itunes” option checked. After I save, I usually go to itunes and the new playlist appears but this time it is NOT working! help please.
I do not want to lose the playlist so I don’t want to re-start the computer. Any ideas?

I’m running Mountain lion. Maybe that’s why? Can you fix this please? My DJAY app is updated and it also happens on my other mac running mountain lion.