Step 1 – Make the shortbread dough
In a large bowl, cream butter and sugar until light and fluffy. Add vanilla. Mix in flour and salt gradually. If the dough is too crumbly, add 1–2 tablespoons of milk until it holds together.

Step 2 – Roll and cut the cookies
On a lightly floured surface, roll the dough to ¼ inch thick. Cut into rings using a 2–3 inch round cutter and a smaller cutter for the center. Transfer to a baking sheet lined with parchment.

Step 3 – Bake and cool
Bake at 350°F (175°C) for 10–12 minutes, or until edges are lightly golden. Cool completely on a wire rack.

Step 4 – Toast the coconut
Spread shredded coconut on a baking sheet and toast at 350°F for 6–8 minutes, stirring halfway, until golden. Watch carefully—it burns quickly.

Step 5 – Make the caramel topping
Melt caramels with heavy cream in the microwave in 30-second intervals, stirring until smooth. Stir in vanilla, salt, and toasted coconut.

Step 6 – Top the cookies
Spoon or spread the caramel-coconut mixture onto each cookie. Press gently to help it adhere. Let set for 10–15 minutes.

Step 7 – Dip and drizzle with chocolate
Melt chocolate and coconut oil (if using) in the microwave until smooth. Dip the bottoms of the cookies, then place on parchment to set. Use a fork or spoon to drizzle the tops with chocolate.

Step 8 – Let cool and enjoy
Allow the cookies to set at room temperature or in the fridge until the chocolate firms up. Then serve, store, or gift!