I’ve plugged in several headsets to my xbox controller and none of them are working

It's possible that there might be a controller update needed, which is why the issue suddenly started to occur. You can check for a controller update in the Xbox Accessories app, or by going to Settings -> Devices & Streaming -> Accessories. Once in the
app click on the three dots under your controller on screen, and see if there's an update available. I believe the current controller firmware is 4.8.1923.0 (But I'm in the Xbox Insider program, so that might vary from the one you see).

If that doesn't work, then can you see if there's some sort of "muted" icon on screen when you plug in your headset? If you start a party, does the ring still light up when you speak, or does it display an error?

It's also worth power cycling your console in these situations, as that can often fix a lot of smaller issues with games loading or OS level issues, there's a guide on how to do that at the following link: https://beta.support.xbox.com/help/hardware-network/power/restart-or-power-cycle-console

It's happening to me as well,but there's no controller updates what should i do?

Thank you, this helped alot

I’ve tried 3 different headsets and none of them are working... pretty sure its the controller.

The headset is brand new. I have trued 4 controllers none of them work. The headset works on my laptop. The microphone with the criss through shows whether or not i have a headset plugged into a controller. Headsets have worked in the past on these controllers.
Believe it to be a microsoft issue. Many people complaining about the same issue online.