These homemade Samoas Cookies combine buttery shortbread with toasted coconut, gooey caramel, and rich dark chocolate. Each cookie has a crisp, pale-golden base topped with a chewy coconut-caramel layer, then dipped and drizzled with chocolate. They’re a delicious homemade version of the classic coconut, caramel, and chocolate cookie.
Add the softened butter and sugar to a stand mixer fitted with the paddle attachment. Beat until light and fluffy.
In a separate bowl, whisk together the flour, baking powder, and salt. Add the dry ingredients to the butter mixture in three additions, mixing after each addition and scraping down the bowl as needed.
Add the milk and vanilla and mix until the dough begins to come together. Divide the dough in half, form each half into a disk, wrap in plastic wrap, and refrigerate for about 1 hour or until firm.
Heat the oven to 350°F. Roll the chilled dough on a lightly floured surface until about 1/8-inch thick, then cut it into rings using a doughnut-shaped cutter or two round cutters.
Arrange the cookies on a parchment- or Silpat-lined baking sheet. Bake for 10 to 12 minutes, rotating the pan halfway through, until the cookies are pale golden. Transfer to a wire rack and cool completely.
Spread the shredded coconut on a parchment-lined baking sheet. Toast at 350°F for about 10 minutes, stirring frequently, until evenly toasted.
Place the caramels, 3 tablespoons whole milk, and 1/4 teaspoon salt in a medium saucepan set over a larger saucepan of simmering water. Stir until completely melted and smooth.
Mix about three-quarters of the melted caramel with the toasted coconut. Spread the reserved caramel over the cooled cookies, then press the coconut-caramel mixture onto the tops. Let the cookies cool for about 30 minutes.
Melt the dark chocolate in a double boiler or microwave. Dip the bottom of each cookie into the chocolate and place it on a wax paper-lined baking sheet.
Use a fork to drizzle the remaining melted chocolate over the tops of the cookies. Let the cookies sit until the chocolate is completely firm.
Notes
Watch the coconut closely while it toasts and stir it often because it can burn quickly.
Keep the shortbread pale golden rather than deeply browned for the best texture.