Position a rack in the center of the oven and preheat the oven to 350ºF. Line a baking sheet with parchment paper; set aside.

In the bowl of a stand mixer, beat the butter for 30 seconds and then add the powdered sugar and cream them together, about 1 minute.

Add the vanilla and the flour until the flour is mostly mixed in. The dough will be shaggy and that’s okay, we’ll work the rest by hand.

Flour a clean work surface. Dump out the dough and pull it together without working it too much, sprinkling with a little bit of flour if it’s sticking.

Roll the dough out until it’s ½ inch thick, using a rolling pin. Using a 2-inch circle cookie cutter, cut out shapes.

Add the cookies to the lined baking sheet, about 1 inch apart and bake the cookies for roughly 13-16 minutes.

Remove from the oven and allow the cookies to cool before attempting to move them to a wire rack.

Combine the unwrapped caramels and the heavy cream in a microwave-safe bowl and zap in 30-second increments, stirring in between until the caramel melts.

Spread the caramel on the cooled cookies using a spoon or a small offset spatula leaving a small rim around the corner.

Allow the caramel to cool for several minutes or if you’re in a hurry, pop the cookies in the freezer for about 5-7 minutes while you prepare the chocolate.

Add roughly ⅔'s of the chocolate to another microwave-safe bowl and melt for 30 seconds, stir and continue to pop into microwave for 10-15 seconds (stirring in between) until the chocolate melts.

Spread the chocolate over the caramel layer. Sprinkle with a pinch of Maldon salt, if desired. Allow the chocolate to harden.