Controller wont connect to headset

Zylu, turn on the 360 by the power button on the console first, not on the controller. Now turn on the headset and sync it up. See if it takes position one. Then turn on the hand controller and see if it grabs position one as well. If both are on the same
position your in buisness. Hope that helps.

In the instructions to the bluetooth headset it says that it will recognize the headset as an external device and will use slot one but some controllers wont allow the headset to be on the same slot as the controller the red brand controllers do not work
with the headset

So I needed up hard wiring my xbox to my internet box. One of my old controllers I got to connect but my headset or my elite controller still wont connect and if I try to connect to wifi it wont. I have tried the hold the power button down for 10 seconds
and still nothing. The xbox I have is the halo 5 collector's edition.

Not all headphones use the same hardware.

See below link for more information on this. (its near the bottom I think)

https://support.xbox.com/xbox-one/accessories/connect-compatible-headset

Some headphone wont work on my controller directly plugged into the controller, but work fine when using the headset adapter.

Have you tried connecting headset to controller with a headset adapter connected to controller. The adapter has volume controls on it.