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 3 increments, add the flour mixture to the creamed butter, mixing between each addition and scraping 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.

Use your hands to divide the dough in half and makes disc like shapes with each one. Wrap them each in plastic wrap and refrigerate until firm, about 1 hour.

Once the dough has chilled, roll each disk out onto a lightly floured surface until it is about 1/8 inch thick.

Cut out as many cookies as possible with a donut shaped cookie cutter. Place the cut out cookies on a Silpat or parchment paper lined baking sheet. Repeat with remaining dough.

Bake the cookies for about 10-12 minutes, rotating the baking sheet halfway through, until the cookies are a pale golden brown. Immediately transfer to a wire rack and cool completely.

Spread coconut flakes on a baking sheet lined with parchment paper. Bake the coconut for about 10 minutes in a 350°F oven until toasted, stirring frequently to ensure even browning and so that it does not burn. Remove from oven and set it aside.

Melt the caramels, milk, and salt on low on the stove. Cook, stirring until the caramels are fully melted.

Remove from heat and combine 3/4 of the caramel mixture with the toasted caramel 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/caramel mixture. Repeat for each cookie. If the coconut/caramel mixture becomes too hard to manage, reheat mixture on very low heat until spreadable again.

Melt the dark chocolate in microwave on on stove on low. Once fully melted, dip the bottoms of the cookies in the chocolate and place them on wax paper. Drizzle some chocolate over the tops of the cookies as well.

Let the cookies sit until chocolate fully hardens.

Helpful tips! *No donut shaped cookie cutter? Use a regular cookie cutter and a small dry spice lid for the smaller hole. *If dough is too firm after being in the fridge, let it rest at room temp for 10 min. *The shortbread should be very pale in color. When in doubt, underbake it! *Coconut burns very quickly so keep an eye on it and stir often! *Spreading the cookies with the reserved 1/4 cup of caramel gives the coconut mixture a sticky base to adhere to.