Preheat oven to 350°F.
For cookies: Place butter and sugar in a stand mixer, fitted with a paddle attachment (or use a hand mixer) and cream together, about 3 minutes or until light and fluffy.
Add vanilla, mix and scrape down the sides of the bowl.
In another bowl combine the flour and salt. With the mixer on low, begin adding the flour. Add until all flour has been used and the mixture just comes together and forms cookie dough. Wrap cookie dough into a disc and chill for at least 30 minutes.
Very lightly flour a clean surface and roll your dough out until ⅛ inch thick.
Cut out 2”-2 ½″ circles in the dough and create holes in the center of each cookie. Place cookies onto a parchment lined baking sheet and chill in the refrigerator for 20 minutes.
Bake cookies for 18 to 20 minutes or until the cookies barely begin to brown around the edge. Transfer cookies to a cooling rack and allow cooling completely (repeat until all cookie have been baked).
For the coconut-caramel topping: Place sugar, cream, butter, and salt into a saucepan over medium heat and stir together. Cook for about 6 to 7 minutes or until the mixture has cooked down and formed a smooth caramel sauce., Fold coconut into the caramel sauce until completely incorporated.
To assemble: Spread 2 teaspoons of the coconut-caramel mixture over each cookie and allow topping to set, about 15 minutes. Dip the bottoms of each cookie (or spread using an offset spatula) in the melted chocolate and place onto a parchment lined baking sheet. Drizzle the remaining chocolate over the cookies and allow the chocolate about 30 minutes to set. Gently remove cookies from parchment sheet and serve. Can store in an airtight container for up to five days.