Headset problem on Xbox controllers

Sounds like a headset or a xbox controller problem ... do u have another controller to try the headset in to see if its the controller that is the problem? Or do u have another headset to plug into the controller to see if the other headset is the problem?

Turn off and disconnect all controllers from the Xbox 360 and disconnect the wireless headsets from the controllers.

Connect the wireless headset to the Xbox 360 using the USB cable. Turn on the wireless headset.

Sync the headset to quadrant 1 by pressing the "Connect" button on the on the Xbox 360. Then press the "Connect" button on the wireless headset for two seconds. Do not continue to press the "Connect" button on the wireless headset, as this will change the
quadrant to which it is connected. If the headset now works without the controllers attached, the problem must be with one of your controllers. If the headset still does not work, then the problem is with the headset.

Just bought a brand new titanfall edition controller and had the same problem. The controller refused to update with the xbox stereo headset hooked up. Looks like it's the headset/adapter that is the problem. I'm going to return the headset and try a different
one.

If you have another headset (even a regular wired headset that comes with an Xbox, or a plain hands-free headset for an old cell phone) you can try that. If headset 2 also has the loose connection problem, then you know it's your controller at fault. If
headset 2 works, then try another controller. If controller 2 also has the loose connection problem then you know it's your headset's wire at fault.

I would definitely try what others above have suggested to isolate the problem - try the headset with a different controller and try a different headset on the same controller to figure out if the problem is the headset or the controller.