Kalibrgun Cricket fill probe oring only survives one fill

I recently bought a used Cricket and I can only fill the the gun up once and the o-ring is damaged. Is this a common issue or is there something wrong with my fill probe. The probe itself looks a little beaten up but not too terrible. I don't know what type of o-ring they are but it feels like silicone. The guy who sold me the gun gave a few. Maybe they are too soft.

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Honestly, those o rings look old as dirt. If the previous owner lived in arid climate it would age out o rings fast. Get new proper sized rings and give them a touch of silicone grease. If somehow this issue still persists, your fill port isn't lining up correctly and is mangling the o rings as the probe is put in.
 
I agree with the guys above. I've had no issues with mine , but mine aren't as old as yours looks. If your replacement o rings were dried out before you put them on they may have cracked when you stretched them putting on probe. When you get the new ones lightly coat with silicone and store in a Zipp lock bag away from heat and sunlight.
 
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FYI, silicone has no practical shelf life limitation. Age isn’t the problem, it’s just that silicone has the poorest tear and abrasion resistance of any common O-ring elastomer. Buna-N or polyurethane will fare much better. However if the problem continues, inspect the fill port with the aid of magnification for a potential burr.