I have problems with my headset or Xbox

Try performing a hard reset EXACTLY like this.

Hold the power button on the console for 8 seconds or until the power shuts down completely. Unplug the power cord from the back of the console for 5 minutes. Plug the power cord back in and restart the console.

If that doesn't help you may need to try an Xbox branded headset.

Can I ask which headset you are using and how it is setup to your controller/console.

Same! I'm also having this problem. My 3.5mm adapter Xbox headset (one I got from the box) doesn't work with my Halo 5 controller, I even got my headset replaced through the Xbox Online Service Centre and the problem still persists. I actually think it's
the controller. I can't really test the headset on another controller since I don't have another one but I bet it's not the headset.

i have the same problem my headset will not insert to my xbox one controller

@DarkThrone I have the same exact problems as you. Using a TB xp400. I've only just got my Xbox One and it's driving me mental. I know it's not a headset problem as I use the headset on my PS4 and it works fine. It's clearly a problem with the adaptor.

As for buying a new headset - I've looked at them and they all say they include the headset adaptor, making me think they'd have the same issues too.