A method for treating a natural drainage passageway in a subject includes forming a cannulated artificial passageway into a subject's sinus cavity through the canine fossa region with a piercing member, the piercing member containing a hollow cannula thereon, the cannula comprising an elongate flexible member having a lumen passing therethrough. The piercing member is removed so as to leave the cannula in place. A balloon dilation catheter is then advanced within the lumen of the cannula so as to place the dilation balloon at least partially across the natural drainage passage in the sinus cavity. The dilation balloon is dilated so as to at least partially expand the natural drainage passageway.