I am hoping this will work with the Jaybird headphones. I considered the Kokkia i10s 30-pin adapter which seems to be popular but I did not want to burden the battery on the classic with that device. I also considered numerous other popular bluetooth 3.5mm transmitters out there among my google searches for ipod classic and Jaybird X3 - like those by TaoTronics. I just like the aesthetic and portability of the Airfly so I decided to try it. Really hope it works out.