Preheat the oven to 350 degrees F (175 degrees C). Line 18 cupcake cups with paper liners.
Beat butter, sugar, egg, and vanilla extract together using an electric mixer in a mixing bowl until smooth.
Sift 1 1/2 cups plus 2 tablespoons flour, baking powder, baking soda, and salt together in a separate bowl. Mix into butter mixture until combined.
Place 1 teaspoon of batter into each of the prepared cupcake cups. Sprinkle each cup with a little sugar.
Bake in the preheated oven until golden, about 10 minutes. Remove from the oven and indent each cup using a teaspoon-sized measuring spoon. Let cool 10 minutes.
While cookie cups cool, beat cream cheese, 1/4 cup plus 2 tablespoons sugar, and egg together using an electric mixer in a mixing bowl until smooth. Place a little more than 1 teaspoon of filling into each cookie cup. Sprinkle with sugar.
Bake in the preheated oven until filling sets, 10 to 15 minutes more. Let cool completely before serving.