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I would also add that lubing up the o ring helps it settle better while tightening down the 2 halves.

Improper torque procedures will often cause misshapen orings or if there is not enough lubricant or surfaces are not clean.

Often times o rings deform under compression for long periods of time. I'm unsure of the diameter options for the military wheels but for heavy equipment in 25" there are 2 different o ring diameters. Using the wrong one usually makes it leak. In heavy equipment the o rings often look t shaped...

First off I believe the wheels are stamped tubeless only. You will rip the stem in a tube because they are not in the correct place. Second I wouldn't crank down the o ring down that hard for the first tightening. I would find them all down hand tight then only go lightly say 50lbs or less till...