Preheat oven to 350°F (175°C).
In a mixing bowl, cream together softened butter and granulated sugar until light and fluffy.
Add egg white and vanilla extract. Mix until well combined.
Stir in flour and baking powder until a soft dough forms.
Roll dough out on a lightly floured surface to 1/4–1/2 inch thickness.
Use a round cookie cutter to cut circles and transfer to an ungreased baking sheet.
Bake for 6–8 minutes, until cookies are puffed and no longer glossy. Do not overbake.
Transfer to a wire rack and cool completely.
In a microwave-safe bowl, heat caramels and milk for 1 minute, stirring at 30 seconds until smooth.
Spoon caramel onto each cooled cookie, spreading almost to the edges.
Refrigerate for 10–15 minutes until caramel is firm.
Melt chocolate chips in 30-second intervals, stirring between each until smooth.
Spread melted chocolate over caramel layer and allow to set completely before serving.