Step 1

To prepare the cookies, whisk together flour, baking powder, and salt and set aside. Mix together butter and sugar in a separate bowl until fluffy. Add flour and mix with until fine crumbs form. Add milk and vanilla and continue to mix until dough comes together. Flatten the dough slightly, wrap it in plastic wrap, and chill for 1 hour OR freeze for 20 minutes.

Step 2

After dough has chilled, roll it out on a flat well-floured surface to about 1/4 inch thickness. (If the dough is too sticky, sprinkle a couple tablespoons of flour over the dough and knead it a few times with your hands. roll it back into a 1/4 inch thick disc.)

Step 3

Use a round cookie cutter to cut as many cookies as you can from the dough. Cut the centers out with a smaller cookie cutter. (*see note for alternative method) Place each cookie onto a greased baking sheet. Press the remaining dough into a ball, roll into a 1/4 inch disc again and repeat cutting process. Do this again until you have used as much of the dough as you can.

Step 4

Bake cookies at 350 for 10-12 minutes until cookies look "dry" and very slightly golden in color. Place cookies (on a baking sheet) in the fridge or freezer.

Step 5

In a medium pan over medium heat, continually stir coconut flakes until lightly browned (about 3-5 minutes). Set toasted coconut flakes aside.

Step 6

In a microwave safe bowl, combine caramels and heavy cream and microwave on high 2 minutes. Stir, and return to microwave for 20 seconds at a time, stirring between each, until caramel is fully melted and smooth. Stir in salt and vanilla.

Step 7

Spread about 1-2 teaspoons of caramel on top of each shortbread cookie. Chill for 2-3 minutes to let the caramel set.

Step 8

Stir coconut flakes into remaining caramel. Spread coconut-caramel mixture onto each cookie. Chill again while you prepare the chocolate.

Step 9

Add chocolate chips to a microwave safe bowl. Microwave on medium power for 2 minutes. Stir, then return to microwave for 20 seconds at a time, stirring between each, until fully melted and smooth.

Step 10

Carefully dip each cookie in the melted chocolate so that the bottom is well-coated. After all cookies have been dipped, drizzle remaining chocolate over the cookies.

Step 11

Store in an airtight container or ziplock bag chilled or at room temperature up to 1 week.