Preheat Oven: Preheat to 350°F (175°C). Line a baking sheet with parchment paper.

Prepare Shortbread: Cream together butter, sugar, and vanilla. Gradually add flour and mix until dough forms. Roll out dough to 1/4 inch thickness and cut into rounds. Place on the prepared baking sheet.

Bake: Bake for 10-12 minutes, or until edges are golden. Let cool.

Make Caramel Layer: Melt caramel candies and cream in the microwave, stirring every 30 seconds until smooth. Spread a layer of caramel on each cooled cookie.

Chill: Refrigerate cookies for 20 minutes to set the caramel.

Melt Chocolate: Melt chocolate chips and coconut oil (if using) in the microwave in 30-second intervals until smooth. Dip each cookie into the melted chocolate and let excess drip off.

Set: Let the cookies set on parchment paper. You can refrigerate them for faster setting.

Serving: Serve once chocolate is fully set and firm.