Controller no longer registering headset after update.

I'm having the same issue.

I haven't had a chance to try the troubleshooting here but maybe you can give it a go?

https://support.xbox.com/en-US/xbox...troubleshoot-xbox-one-chat-headset-windows-10

You should use the Reddit XBox Insiders Forum for this issue.

If you have a play /charge uSB cable connect it to the controller and console and try turning the console on with the controller. You may be prompted to update the controller firmware.

Are you in the Insiders?

Have you done a Full shutdown and restarted the console?

Hi CoolBaz5000,

Thank you for coming to the forums. There have been reports of third party headsets not being detected when plugging in through the 3.5 mm port. It's still not known if its a hardware issue with the port itself or simply a controller firmware update that
caused the 3.5 mm port to no longer register with certain third party headsets, but this is still being investigated. If the headset works on other devices, then the issue is with the controller's 3.5 mm port not recognizing that headset as compatible. The
only solutions at the moment are to replace the controller and try another one to confirm it's the controller port or purchase an Xbox One Stereo headset adapter that comes included with the

Xbox One stereo headset, it is not sold separately.

I agree. My headset often doesnt register but updating your controller even when it says no update required fixes it every time.