In a medium size bowl, cream together the butter and sugar until light and fluffy
In separate bowl, whisk together the flour & baking powder. In three increments, add the flour mixture to the creamed butter. Mix between each addition and scraping down the sides of the bowl when necessary. Add the milk and vanilla extract,blending until combined and the dough comes together.
Divide the dough in half, pressing it together to compact it into two disks. Wrap the disks securely in wax paper and refrigerate them until firm, about 1 hour.
Preheat oven to 350 degrees.
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. Place the cut out cookies on a parchment paper lined baking sheet and repeat with remaining dough.
Bake the cookies for 10 to 12 minutes, rotating the baking sheet half way through, until the cookies are pale golden brown. Transfer the cookies to a rack to cool completely.
Making the coconut topping. This step should be done while the dough is in the refrigerator.
Spread the coconut flakes onto a baking sheet lined with parchment paper. Bake the coconut for about 10 minutes in a 350 oven until toasted. Stir frequently to ensure even browning. Remove the toasted coconut and let cool.
Melt the caramels and milk in a double boiler. Cook stirring, until the caramels are fully melted. Remove the sauce pot from the heat and combine 3/4 if the caramel with the toasted coconut.
Carefully spread the remaining 1/4 cup of caramel atop the 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, return it to the double toilet and warm until spreadable.
Melt dark chocolate in microwave safe bowl at 15 second intervals. Then stir & continue melting. Dip bottoms of the cookies in the chocolate and place them on a wax paper lined baking sheet.. Use fork to drizzle tops with chocolate.