Eu não sei o suficiente sobre 3.5, então minha resposta só irá abordar o Pathfinder.
As regras para a habilidade wirlwind parecem não resolver isso. No entanto, como GM, eu trataria o redemoinho como sendo similar ao do paredão de vento soletrar:
An invisible vertical curtain of wind appears. It is 2 feet thick and of considerable strength. It is a roaring blast sufficient to blow away any bird smaller than an eagle, or tear papers and similar materials from unsuspecting hands. (A Reflex save allows a creature to maintain its grasp on an object.) Tiny and Small flying creatures cannot pass through the barrier. Loose materials and cloth garments fly upward when caught in a wind wall. Arrows and bolts are deflected upward and miss, while any other normal ranged weapon passing through the wall has a 30% miss chance. (A giant-thrown boulder, a siege engine projectile, and other massive ranged weapons are not affected.) Gases, most gaseous breath weapons, and creatures in gaseous form cannot pass through the wall (although it is no barrier to incorporeal creatures).
Ênfase minha.