Not a stupid question at all OP. I have a CS drop-forged hunter, which is a very cool little blade that I would like to carry more, but the sheath is the exact same type you have there, the bottom part is nice and the blade locks in well, but with the flexible top section the whole sheath pulls up unless you have something securing it at the bottom, so it takes two hands basically to pull it, don't know why they chose this design, makes no sense at all.
What I would like to see, is a hard plastic upper section you could bolt to the sheath that replaces the flexible stuff, don't know if that exists or not.