Preheat oven to 325°F (160°C). Toast coconut on a baking sheet for 10-15 minutes, stirring frequently until golden. Let cool.

Increase oven to 350°F (175°C). Cream softened butter and sugar until light and fluffy. Beat in vanilla extract.

Whisk flour and salt together. Gradually mix into the wet ingredients until a dough forms. Add milk if dough is too crumbly.

Chill dough for 30 minutes. Roll out to 1/4-inch thickness and cut into 2-inch rings with a 3/4-inch center hole.

Bake cookies on parchment-lined sheets for 10-12 minutes until edges are pale golden. Cool completely on a wire rack.

Melt unwrapped caramels, heavy cream, and salt in the microwave in 30-second intervals until smooth.

Spread a thin layer of plain melted caramel onto each cookie. Fold toasted coconut into the remaining caramel.

Press the sticky coconut-caramel mixture onto the top of each cookie ring. Allow to set.

Melt chocolate chips with coconut oil until smooth. Dip the bottom of each cookie into the chocolate and place on parchment.

Transfer remaining melted chocolate to a bag, snip the corner, and drizzle over the top of the cookies. Chill to set.