Heat oven to 350ºF.
In a small bowl, combine sugar and cinnamon. Brush outside of tortillas with melted butter.; sprinkle with cinnamon-sugar, covering the tortillas completely. (Discard any extra cinnamon-sugar or reserve it for another use.) Arrange the tortillas on a baking sheet and bake for 10 minutes, or until the top edge begins to brown. The tortillas will still be soft when you take them out of the oven, but they’ll crisp up as they cool. Let cool completely.
In a small saucepan, heat the cranberry sauce over low heat. Stir in the honey, vanilla, and two tablespoons water. Let cool.
To serve, scoop two small scoops of ice cream into each tortilla cup. Top with cranberry sauce.