Directions

1. 1

   In the bowl of an electric mixer, cream together the room-temperature butter and sugar for 2-3 minutes until the mixture is light and fluffy.

2. 2

   In a separate medium bowl, whisk together the flour, baking powder, and salt until well combined.

3. 3

   Add the flour mixture to the creamed butter in 3 additions, mixing on low speed and scraping down the sides of the bowl between each addition until just combined.

4. 4

   Add the milk and vanilla extract to the dough and blend on low until the mixture just comes together. Form the dough into a disk, wrap it tightly with plastic wrap, and refrigerate for about 1 hour until chilled.

5. 5

   Preheat the oven to 350 degrees Fahrenheit and line a baking sheet with parchment paper or a Silpat mat.

6. 6

   On a lightly floured surface, roll out the chilled dough to about 1/8 inch thickness. Using a donut-shaped cookie cutter (or two round cutters of different sizes to create rings), cut out cookies and place them on the prepared baking sheet.

7. 7

   Bake for 10-12 minutes, rotating the baking sheet halfway through, until the cookies just begin to turn golden brown. Avoid overbaking to keep them tender. Cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.

8. 8

   While the cookies cool, toast the shredded coconut in a dry medium saucepan over medium-low heat for 5-10 minutes, stirring frequently to prevent burning. Set aside to cool.

9. 9

   In a double boiler, gently melt the caramels with 1-1/2 tablespoons milk and the salt, stirring until completely smooth and melted.

10. 10

    Remove the caramel mixture from heat. In a large bowl, combine 3/4 of the caramel mixture with the toasted coconut and mix well.

11. 11

    Spread a small amount of the remaining caramel onto the top of each cooled cookie to act as an adhesive. Press a portion of the coconut-caramel mixture onto the caramel layer of each cookie. If the mixture becomes too firm to work with, microwave for 10 seconds until it reaches a spreadable consistency. Let the cookies set at room temperature for at least 30 minutes.

12. 12

    Place the semisweet chocolate in a microwave-safe bowl and melt it in 30-second intervals, stirring vigorously after each interval until completely smooth.

13. 13

    Dip the bottom of each cookie into the melted chocolate and place on a wax-paper-lined baking sheet. Drizzle additional chocolate over the tops of the cookies if desired.

14. 14

    Refrigerate the cookies for 10-20 minutes until the chocolate is completely hardened. Store in an airtight container.