1. Preheat and Prepare:
Start by preheating your oven to 350°F. This ensures that the oven is at the right temperature when you’re ready to bake the cookies, helping them bake evenly. While the oven is heating, line a baking sheet with parchment paper or simply grease the baking sheet lightly to prevent the cookies from sticking. Having everything ready to go will make the baking process smoother and faster.

2. Cream the Butter and Sugar:
In a large mixing bowl, cream together the softened butter and granulated sugar until the mixture is light and fluffy. This is a crucial step, as creaming the butter and sugar properly incorporates air into the dough, giving the cookies a light texture. Use a hand mixer or a stand mixer with the paddle attachment to make this step easier, but if you don’t have one, you can always do it by hand with a whisk or spatula. Creaming the butter and sugar also helps dissolve the sugar into the butter, making the dough smoother.

3. Add the Wet Ingredients:
Mix in the vanilla extract and egg white until well combined. The egg white will help the dough come together and add to the overall texture of the cookies. Make sure to mix until the egg and vanilla are fully incorporated into the butter and sugar mixture, creating a smooth, cohesive dough.

4. Combine the Dry Ingredients:
Gradually add the flour and baking powder to the wet mixture, mixing thoroughly until the dough forms. The dough should be slightly sticky but still manageable. If it feels too soft or sticky, you can add a little more flour, a tablespoon at a time, until the dough reaches the right consistency. Be careful not to add too much flour, as this can make the cookies dense and dry.

5. Shape the Cookies:
Roll out the dough to a thickness of about 1/4 to 1/2 inch. Using a round cookie cutter, cut out circles of dough and carefully transfer them to the prepared baking sheet. If you don’t have a cookie cutter, you can use the rim of a glass or simply shape the dough with your hands. Make sure to leave some space between the cookie cups so they don’t stick together while baking.

6. Bake to Perfection:
Bake the cookies in the preheated oven for 6-8 minutes. Keep an eye on them, as baking times can vary slightly depending on your oven and the thickness of the cookies. The cookies are done when they are puffed up and golden around the edges, with no glossy spots in the center. Be careful not to overbake, as this can result in dry cookies. Remove them from the oven and allow them to cool completely on a wire rack before proceeding to the next step.

7. Prepare the Caramel:
While the cookies cool, unwrap the caramels and place them in a microwave-safe bowl. Add the milk and microwave the mixture in 30-second intervals, stirring after each interval. Continue heating and stirring until the caramels are completely melted and the mixture is smooth. Be careful not to overheat the caramel, as it can burn or seize up. If you find the caramel too thick, add a little more milk to reach your desired consistency.

8. Add the Caramel Layer:
Once the cookies have cooled, use a spoon to carefully place a few teaspoons of the melted caramel on top of each cookie. Spread the caramel almost to the edges of the cookie, leaving a small border around the outside. The caramel should be thick and gooey, but it will spread easily over the surface of the cookie. Be sure to evenly coat each cookie with caramel for a consistent texture.

9. Chill the Cookies:
Place the cookies with the caramel in the refrigerator for 10-15 minutes or until the caramel is fully set. This step is important to ensure that the caramel hardens enough to hold its shape when the chocolate is added on top. You can also chill the cookies for longer if you prefer a firmer caramel layer.

10. Melt the Chocolate:
In a microwave-safe bowl, melt the milk chocolate chips in 30-second intervals, stirring after each session. Be patient and stir thoroughly after each interval to ensure the chocolate melts smoothly. If the chocolate seems too thick, you can add a small amount of vegetable oil or butter to help thin it out.

11. Add the Chocolate Topping:
Once the chocolate is fully melted and smooth, use a spoon or spatula to spread a thin layer of chocolate over the cooled caramel layer on each cookie. The chocolate should cover the caramel completely, creating a smooth, shiny finish. Allow the chocolate to set completely before serving. You can place the cookies back in the fridge to speed up the setting process if needed.