Headset not picking up

If you have tried the troubleshooting tips and are still having issues then your headset jack has probably shifted on the circuit board. I've been having this issue for a while now and just found out that the jack isn't even soldered to the board. The
only fix for it is to make a warranty claim if you are still covered or crack the controller open and solder it in place. It is completely up to you if you decide to crack one open that is still under warranty. It's a known design flaw that still hasn't
been addressed. There are videos on YouTube if you decide to fix it yourself.

Im sorry to hear your having this issue, it appears to be something a lot of people are experiencing. I would check to see if the controller needs updated. Try power cycling your console. Then here are some troubleshooting ideas you can try.

https://support.xbox.com/en-US/xbox-one/accessories/wired-headset-help

Im having the same problem. I bought hyperx cloud headset and it wont work. Driving me nuts.

I have the same problem as him. Multiple controllers, tried different headsets. Tried every troubleshooting tip that Microsoft gives. It's not a console issue, it's a hardware issue in the controller. A KNOWN issue according to the Microsoft tech support
guy I spoke with on the phone. Only fix that Microsoft has for it is to swap out controllers for new ones that will eventually start having the same issues. I did not post any actual links, just told him to do some research. This is yet another reason why
Microsoft is losing my business. You guys can't handle someone putting the truth out there about a manufacturing/design flaw that still has not been addressed.

Hey there Vaden thanks for the information.

However we here on the Xbox Forums do not condone any self repairs: Please do not discuss or post links to any topic that could violate the Terms Of Use. Including any threads or posts regarding modifying the way your Xbox operates such 'modding' and/or
'chipping' your Xbox or otherwise altering the way it is intended to operate.

Also, as stated on our
Xbox Services Terms & Conditions (17. LIMITED POST-SERVICE WARRANTY) damage caused by repairs or modifications done by someone other than Microsoft or a Microsoft authorized service provider.

As stated by the OP, multiple Xbox Controllers have been checked so we believe the problem might be on the OS of the console so the best course of action would be (as stated by fellow XBF Steven R) to perform a Soft Factory reset.