Cut the faces before adding cheese
Make the face cutouts while the tortillas are flat and dry. Keep the pieces fairly simple, leaving enough tortilla between the openings to lift each top without tearing it. The two uncut tortillas form the bottoms, so place those on the lined tray before dividing the cheese. A narrow border gives the melted cheese a little room without losing the pumpkin face.
Check the quesadillas from the early end of the baking range if your tortillas are thin. The goal is melted cheese with crisp edges, not a deeply browned face. Let them stand as directed before moving to plates. Cut on a board rather than on the baking tray, and offer any additional accompaniments separately so the warm tortilla surfaces stay exposed.
