Cookie Ingredients
1 cup butter, softened
1/2 cup sugar
2 cup all purpose flour
1/4 teaspoon baking powder
1/2 teaspoon salt
1/2 teaspoon pure vanilla extract
1-2 tablespoons milk
Topping Ingredients
3 cups shredded coconut
12 ounces chewy caramels
1/4 teaspoon salt
3 tablespoon milk
8 ounces dark or semi-sweet chocolate
Directions

Place a rack in the middle of the oven and preheat to 350 degrees F.
In a large mixing bowl, cream together butter and sugar. Mix in flour, baking powder and salt at a low speed, followed by the vanilla and milk, adding in the milk as needed to make the dough come together without being sticky. Add in a bit of extra flour if your dough is very sticky.
Roll the dough (working in two or three batches) out between pieces of wax paper to about 1/4-inch thickness (or slightly less) and use a 1 1/2-inch cookie cutter to make rounds. Place on a parchment lined baking sheet and use a knife, or the end of a wide straw, to cut a smaller center hole. Repeat with remaining dough. Bake cookies for 10-12 minutes, until bottoms are lightly browned and cookies are set. Cool for a few minutes on the baking sheet then transfer to a wire rack to cool completely.
Preheat oven to 300. Spread coconut evenly on a parchment-lined baking sheet and toast 20 minutes, stirring every 5 minutes, until coconut is golden. Cool on baking sheet, stirring occasionally. Set aside.
Unwrap the caramels and place in a large pot with salt and milk. Cook over low heat stirring frequently until caramel has melted. When smooth, fold in toasted coconut with a spatula. Using the spatula or a small offset spatula, spread topping on cooled cookies, using about 2-3 teaspoons per cookie.
While topping sets up, melt chocolate in a double boiler over low heat on the stove. Dip the base of each cookie into the chocolate and place on a clean piece of parchment paper. Transfer all remaining chocolate into a piping bag and drizzle finished cookies with chocolate. Let chocolate set completely before storing in an airtight container.