I preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper. In a mixing bowl, I cream ½ cup softened butter and ½ cup granulated sugar with a mixer on medium-high for 2–3 minutes until light and fluffy. I add 1 egg white and 1 tsp vanilla extract, mixing until smooth. I stir in 1½ cups flour and 1 tsp baking powder until a soft, pliable dough forms.

I roll the dough to ¼–½ inch thickness on a lightly floured surface. Using a 2½-inch round cookie cutter, I cut out circles and place them on the baking sheet. I bake for 6–8 minutes until puffy and no longer glossy, then transfer to a wire rack to cool completely.

In a microwave-safe bowl, I combine 20 soft caramels and 1 tbsp milk. I microwave for 1 minute, stirring halfway, until smooth. I spoon ~1 tsp caramel onto each cooled cookie, spreading it nearly to the edges. I chill the cookies in the fridge for 10–15 minutes to set the caramel.

I melt 2 cups milk chocolate chips in a microwave-safe bowl in 30-second intervals, stirring until smooth. I spread a thin layer of chocolate over the set caramel on each cookie. I let the chocolate set at room temperature or refrigerate for 10 minutes for faster setting.

I serve the cookies at room temperature, savoring their chewy, chocolaty goodness.