Update: Got to my post dated 2/8/2020 for solution. I recently got one of the new Boss Waza Air Headphone sets, and it is really great. Sound, functionality, and a decent fun factor! I received it about the same time my SC594 arrived, so we all got to know one another like a happy family. As my recently documented guitar trading frenzy concluded, I became the proud new owner of a 2018 Silver Sky. Also a fun guitar, but in a completely different direction, so I wanted to check it out with the headphone setup. It appears that Boss was not aware of the redesigned jack plate of the Silver Sky, and the transmitter will not fit into the well there. You can force it, but as that wouldn't be in the best interests of either end, I elected not to go that route. I'll likely solder up a little 1/4 male by female adapter cable to make it work, but I thought I would pass this along in case others were considering the purchase and the SS was your only/main guitar.