Step 1: Make the Cookie Base

1. Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
2. In a mixing bowl, cream together the butter and sugar until light and fluffy. Add the vanilla extract and mix until combined.
3. Gradually add the flour and salt, stirring until a soft dough forms.
4. On a lightly floured surface, roll out the dough to a 1/4-inch thickness. Use a round cookie cutter to cut out cookies, then use a smaller cutter to remove the center (a bottle cap works in a pinch).
5. Arrange the cookies on the prepared baking sheet and bake for 10–12 minutes or until the edges are lightly golden. Cool completely on a wire rack.

Step 2: Toast the Coconut

1. Spread the shredded coconut evenly on a baking sheet.
2. Bake in the preheated oven for 5–7 minutes, stirring halfway through to ensure even toasting.
3. Remove from the oven once the coconut is golden brown and fragrant. Set aside to cool.

Step 3: Prepare the Caramel

1. In a microwave-safe bowl, combine the soft caramels and milk. Microwave in 20-second intervals, stirring after each, until smooth and fully melted.
2. Stir in the toasted coconut until evenly combined.

Step 4: Assemble the Cookies

1. Spoon a generous layer of the caramel-coconut mixture onto the top of each cookie, spreading it evenly.
2. Let the topping set for about 10–15 minutes before proceeding.

Step 5: Add the Chocolate

1. Melt the semisweet chocolate chips in a microwave-safe bowl, heating in 20-second intervals and stirring until smooth.
2. Dip the bottom of each cookie into the melted chocolate and place it on a piece of parchment paper to set.
3. Transfer the remaining melted chocolate to a piping bag (or a zip-top bag with the corner snipped) and drizzle chocolate over the top of the cookies for that classic Samoas look.

Step 6: Cool and Serve

Allow the cookies to cool completely at room temperature until the chocolate is firm. Store the finished cookies in an airtight container for up to a week—or enjoy them right away!