Step 1: Prepare the Cookie Dough

Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper to prevent sticking. In a large mixing bowl, combine 2 cups all-purpose flour, 1/2 cup sugar, and 1/2 teaspoon salt. Add 1 cup cold butter cut into cubes. Mix using a pastry cutter or your hands until the mixture resembles coarse crumbs.

Step 2: Add Liquids and Form Dough

Stir in 2 tablespoons of milk and 1/2 teaspoon vanilla extract. Mix until the dough starts to come together into a ball. You may need to use your hands to knead it slightly.

Step 3: Roll and Cut the Dough

Roll the dough out onto a lightly floured surface to about 1/4-inch thickness. Use a round cookie cutter to cut out circular shapes. Then use a smaller round cutter to create a hole in the center of each circle. Transfer the cookie dough to your prepared baking sheet.

Step 4: Bake the Cookies

Bake for 10-12 minutes or until the edges are golden brown. Allow them to cool completely on a wire rack.

Step 5: Prepare the Caramel Coconut Topping

In a saucepan, melt 20 soft caramel candies with 3 tablespoons heavy cream over low heat, stirring constantly until smooth. Stir in the 1 1/2 cups toasted shredded coconut until well combined.

Step 6: Top the Cookies

Spread the caramel-coconut mixture generously over the cooled cookies. Let the cookies set for about 10 minutes to firm up the topping.

Step 7: Add the Chocolate Coating

Melt 1 cup semi-sweet chocolate chips and 1 teaspoon coconut oil in a microwave-safe bowl, stirring every 20 seconds until smooth. Dip the bottoms of each cookie into the melted chocolate and drizzle more over the top for a decadent finish.

Step 8: Set and Serve

Allow the cookies to set completely at room temperature or refrigerate them for a quicker set. Enjoy your Samoa cookies once they’re fully hardened!