Add the soft butter to a mixing bowl along with the powdered sugar. Beat with the paddle attachment of a stand mixer, or a hand mixer, until fully combined and fluffy, about 1 minute.

Scrape the sides of the bowl and add the vanilla, flour, and salt.

Continue to mix at low/medium speed until the dough comes together.

Divide the dough into 2 and wrap in plastic. Refrigerate 1 hour. Preheat the oven to 350 degrees.

Once chilled, roll the dough between 2 pieces of parchment paper until 1/4 inch thickness.

Cut into circles (or the classic donut shape if desired) and add to a baking tray lined with parchment or silicone baking mats.

Bake 10 to 12 minutes, or until the edges are just lightly browned.

In a glass, or microwave safe bowl, combine the unwrapped caramels and heavy cream.

Microwave for 2 minutes.

Stir, and return to the microwave for 15 seconds at a time, stirring between each reheat, until the caramel is melted.

Stir in the salt and vanilla extract.

Reserve 1/4 cup of caramel for later use.

Stir in the toasted coconut flakes into the rest of the caramel mixture.

Spread roughly 1 teaspoon of the reserved caramel onto the top of each shortbread cookie.

Spread 1 heaping spoonful of the coconut caramel topping directly on top of each cookie.

Melt the chocolate inside a glass bowl, or zip top bag. Drizzle each cookie with chocolate and allow to set before serving.