Replacing Gaskets on 90 degree oil filter adapter

Double check the bolt for twisting . It is hollow and the oil flows through it. They can be damaged from overtightening.
Thanks. I doubt its ever been removed before. Hopefully the previous owner didnt try tightening the bolt down ans bend it like you mentioned. How common is it for the bolt to be damaged? Now im wondering if I buy anotjer bolt so if has been damaged I am able to put it back together right away.