Cream the butter and salt in a stand mixer with the paddle attachment, for 2-4 min. Add both sugars, milk, and vanilla extract. Beat again for 1-2 minutes.
1/2 cup unsalted butter, room temperature, 1/4 tsp. salt, 1/3 cup granulated sugar, 2 Tbsp. powdered sugar, 1 Tbsp. whole milk, 1/2 tsp. vanilla extract
Add the flour and baking soda on low speed just until the dough comes together.
1 cup all purpose flour, spooned and leveled, 1/4 tsp. baking soda
Bring the dough together into a disk. Place on a sheet of parchment paper, place another sheet of parchment on top and roll out the dough between the parchment. Roll it out about ¼ inch thick. Place on a cookie sheet, and chill for at least 1 hour or up to overnight in the fridge.
Preheat the oven to 350°F.
Toast the coconut. Pour the coconut onto a baking sheet and place it in the oven to toast for ~10-15 minutes, stirring frequently to prevent burning. Depending on your oven, this may take longer or faster so be sure to keep a close eye on it! Once toasted, remove to a parchment-lined baking sheet to cool. You want to move it to another sheet pan so the residual heat doesn’t continue to toast the coconut.
3 1/2 cups shredded sweetened coconut flakes
Once the cookie dough has chilled, peel back the top piece of parchment. Cut out the cookies using a 2-inch circular cookie cutter or a donut-shaped cookie cutter. If using just a regular 2-inch circular cookie cutter, you’ll need to use a piping tip to cut out a small circle in the middle. Place the cut-out cookies on a parchment-lined baking sheet and bake for ~8-10 minutes or until the edges just start to become golden. Cool on the cookie sheet for a few minutes, then place on a wire cooling rack.
Rework the scraps, re-roll between the parchment, and chill again until firm enough to make more cutouts. You should be able to yield ~22-25 cookies.
Unwrap the caramels and place in a microwave-safe bowl. Add the heavy cream. Melt in the microwave in increments until melted. Add a touch more heavy cream if needed to get a good consistency.
15 oz. caramels, 2-3 Tbsp. heavy cream
Pour a majority of the caramel into the toasted coconut. Reserve just about ¼-⅓ cup to the side. Mix the caramel into the toasted coconut. It will be nice and sticky but thoroughly combined.
Add a thin layer of the reserved caramel to the shortbread cookie to act as the glue for the coconut caramel mixture so it can stick. Use a spoon to spread it around evenly. This process can get a bit messy, take your time.
Add a mound of the coconut mixture to each cookie ring, pressing it down slightly. I use my fingers for this process. Once again, a little messy, but not bad. Wash your fingers if they get too sticky and then continue mounding the coocnut on. Allow the coconut to set up ~15-30 minutes.
Melt the chocolate and oil in the microwave.
10 oz. bag Ghirardelli dark chocolate melting wafers, 1 tsp. oil (canola or vegetable)
Using a fork, dunk the bottom half of each cookie into the melted chocolate. Tap off excess and then place cookies on a Silpat-lined baking sheet. Repeat with remaining cookies.
Drizzle chocolate on top of cookies. I like to get a fine drizzle over the tops by just placing the remaining chocolate in a ziplock baggie, cutting off one of the corners, and drizzling it over the top.
Allow to set up, and enjoy! Yay you did it!