Make the shortbread base:
Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper.
In a large bowl, cream together butter and sugar until light and fluffy. Mix in vanilla.
Add flour and salt and mix until dough forms.
Roll out dough to about 1/4-inch thickness. Use a round cookie cutter (about 2 inches) to cut out cookies. Use a smaller cutter or piping tip to cut out a center hole.
Place cookies on the prepared baking sheet and bake for 10–12 minutes, until lightly golden. Let cool.

Toast the coconut:
Spread coconut evenly on a baking sheet and toast in the oven for 5–10 minutes, stirring halfway, until golden brown. Watch closely so it doesn’t burn.

Make the caramel topping:
In a microwave-safe bowl, melt the caramels with milk in 30-second bursts, stirring in between, until smooth. Stir in salt and toasted coconut.

Assemble the cookies:
Spoon the coconut-caramel mixture onto the tops of the cooled cookies, gently pressing it on. Let set for a few minutes.

Dip and drizzle with chocolate:
Melt the chocolate in the microwave or over a double boiler. Dip the bottoms of each cookie into the chocolate and place on parchment to set.
Use a spoon or piping bag to drizzle more chocolate over the top of each cookie. Let everything set completely before serving or storing.