How can a headset cause continuous transmission (PTT blocked)?
Apparently the tip connection is being grounded activating the PTT. From the photo the only thing that could possibly be a problem is the Compilot plug being a tiny bit longer than the DC. But the detent in the tip is what should decide where the plug sits in the jack and that looks fine. It almost has to be a wiring problem in the Compilot. If you have a multimeter check for continuity between the barrel and the tip. There should be no continuity unless a PTT button is being pressed.