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I have a plethora of dental work a bridge couple posts one implant fillings all over the place. Never had what I’d call tooth squeeze I do get jaw fatigue about 45 to 50 minutes into a dive. I have a molded mouthpiece and dislike diving with rental gear for this reason above most maybe a customer mouthpiece may be of use to you.
 
On my second OW check dive I experienced what I thought was tooth squeeze. It basically felt like my molars in my upper jaw were going to explode out of my head. It was very painful and lasted the rest of the day. I thought it was my teeth but I found out it was actually my sinuses. Now that I'm not such a green diver I notice better when that feeling is coming on and with a pinch of the nose and a somewhat forceful puff of air I can clear the sinus squeeze before it feels like my teeth want to explode.
 
Tooth squeeze can occur with a cracked/loose filling or abscess. In either case there is trapped gas.
 
https://www.shearwater.com/products/perdix-ai/

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