ok so option #1 is get a smaller fitting, say 1/8" and get an adapter bushing (threaded insert?) in order to be able to tighten to the right location

option #2 i'm not real sure I understand...what would a 1/4" to 3/8" npt adapter bushing look like?

experience is where I am lacking, but it definately seems like the right direction is not tight enough and it doesn't allow for one more complete turn. I don't have my degree in experince yet