Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper to prevent sticking.
In a large bowl, cream the softened butter and granulated sugar together until the mixture is light and fluffy.
Mix in the vanilla extract. Then, gradually add the flour and salt, mixing until a soft dough forms.
Roll out the dough on a floured surface to about 1/4-inch thickness. Use a 2-inch cookie cutter to cut circles, and a smaller cutter to create a hole in the center of each.
Place the cookies on the prepared baking sheet and bake for 10–12 minutes, or until the edges are lightly golden. Let them cool completely on a wire rack.
While they cool, spread the shredded coconut on a baking sheet and toast it in the oven for 5–7 minutes, stirring occasionally until it turns golden brown.
In a microwave-safe bowl, combine the soft caramels and milk. Microwave in 30-second bursts, stirring until melted and smooth.
Mix the toasted coconut into the caramel until well combined. Spread this gooey mixture onto the cooled cookies.
Let the cookies sit for 10 minutes to set.
Melt the chocolate chips in a microwave-safe bowl in 30-second intervals, stirring every time until smooth.
Dip the bottom of each cookie into the melted chocolate and place them on a parchment-lined tray. Drizzle the remaining chocolate over the tops of the cookies.
Let the cookies set at room temperature or refrigerate for about 15–20 minutes until the chocolate hardens.
