Currently using Steelseries Arctis Nova 7x. Best sound and mic quality of any headset I've ever owned. The problem is they make my ears sore after wearing them for any longer than like 2 hours.

I've tried HyperX CloudX Flight - Also good sound and mic quality, but I've had 3 of these so far (only paid for 1, got the other 2 as replacements) and they all developed the same issues. Headset will randomly turn my voice robotic for the people I'm chatting with, and I'll have to restart the headset. When it comes back on the mic monitoring doesn't work so I have to restart it again. The mic monitoring also doesn't work randomly when I turn them on.

Other ones I've looked into:

New Turtle Beach Stealth Pro - Seemed like a really good option, but I didn't want to pay $300 for a headset so was waiting for a sale. They went on sale a few weeks ago for like $250 so I was going to bite the bullet but read the reviews. Apparently the seam on the headband comes apart easily, and there are even lots of review photos where the ear cups fall off or break.

Audeze Maxwell - Seems like the best quality headset for Xbox out there. Again don't really want to pay the $330 that this one costs, but I would do it if it's worth it and would last. The problem is, apparently there's a common issue where the right ear receiver starts losing audio a few months in, and sometimes they both get crackly noises. IMO if a headset is over $300 these issues shouldn't be common.

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So any recommendations would be welcome. My requirements are it needs to be wireless and it needs to have good mic monitoring (lets you hear your own voice). I guess I could make wired work, but all the wired Xbox headsets I see don't connect through a USB, only through a 3.5 mm jack on the controller, so that means the headset isn't really powered so the mic monitoring doesn't work on those. An app to customize audio mixing and turn up the level of mic monitoring is a plus, but not required if those qualities are good on default. And finally, comfort is a big one although I realize this will be hard for people to recommend as head and ear shapes/sizes vary a lot between people.

For the time being I'm sticking with the Steelseries but it is really uncomfortable. Might just try out the regular Xbox Wireless headset. It's only $90 (and cheaper on sale) and I had one of those like a few years back and it was pretty comfortable from what I remember. Ended up giving it to a friend when I upgraded. Can't remember how good the mic monitoring was on those though, and they could have changed since then.