For the cookies
1 cup (2 sticks) unsalted butter, at room temperature
1/2 cup sugar
2 cups all-purpose flour
1/4 teaspoon baking powder
1/2 teaspoon salt
2 Tablespoons milk
1/2 teaspoon vanilla extract
For the coconut topping
3 cups shredded sweetened coconut
15 ounces store-bought or homemade soft caramels
3 Tablespoons milk
1/4 teaspoon salt
8 ounces dark chocolate
First, make the cookies. Preheat the oven to 350F. Line cookie sheets with silpat or parchment paper.
In the bowl of a stand mixer fitted with the paddle attachment, cream together the butter and sugar until light and fluffy. In a separate bowl, whisk together the flour, baking powder and salt. In three increments, add the flour mixture to the creamed butter, mixing between each addition and scraping down the sides of the bowl as necessary. Add the milk and vanilla extract, blending until combined and the dough begins to come together in large pieces. Divide and flatten into two disks. Wrap the disks securely in plastic wrap and refrigerate them until firm, about 1 hour.
Once the dough has chilled, roll each disk out onto a lightly floured surface until it is 1/8-inch thick. Cut out as many cookies as possible with a doughnut-shaped cookie cutter. Bake the cookies for 10 to 12 minutes. Transfer the cookies to a wire rack to cool completely.
Next, make the coconut topping. Spread the coconut flakes onto a baking sheet lined with parchment paper. Bake the coconut for about 10 minutes in a 350F oven until toasted, stirring frequently to ensure even browning and so that it does not burn. Remove the toasted coconut from the oven and set it aside.
Melt the caramels, milk and salt in a double-boiler by placing the caramels in a medium saucepot set over a large saucepot of simmering water. Cook, stirring, until the caramels are fully melted. Remove the saucepot from the heat and combined 3/4 of the caramel with the toasted coconut in a large bowl.
Carefully spread the remaining 1/4 cup of caramel atop the cooled cookies then press on a portion of the coconut mixture. Let the cookies cool for 30 minutes. If the caramel-coconut mixture thickens too much at any point while pressing it onto the cookies, return it to the double-boiler and warm it until it’s spreadable again.
Melt the dark chocolate in a double-boiler. Dip the bottoms of the cookies in the chocolate and place them on a wax paper-lined baking sheet. Use a spoon or a squeeze bottle to drizzle the tops with chocolate. Let the cookies sit until the chocolate hardens fully.