Chosen Solution
My headset works, I try plugging it into my controller over and over but it doesn’t seem to resolve itself. It works on my brothers controller but not mine, I’ve tried to update it but it doesn’t need updating
Hi, Has it worked OK before with the controller? What is the model number of the controller? You may have a faulty or loose headphone jack. (or stereo headphone jack adapter if this is what you are plugging into) Here is a link to the ifixit Xbox One Wireless Controller repair guides for the various models. These show how to open the controller so you can access the motherboard to inspect the headphone socket, (if it is the headphone jack that you are plugging into and not the stereo headset adapter)
(click on image to enlarge for better viewing) If it is faulty, depending on the model number ifixit has some headphone jack assembly parts available