Toast the coconut: Add the coconut flakes to a skillet over medium heat and cook for 5 to 7 minutes, stirring constantly, until the coconut is evenly toasted and golden. Remove from heat and allow it to cool.
Melt the caramel: Place the caramel baking bits and heavy cream in a microwave-safe bowl. Microwave in one-minute intervals, stirring each time, until the caramel is completely melted and smooth.
Combine caramel and coconut: Stir the toasted coconut into the melted caramel until everything is evenly coated.
Assemble the cookies: Spoon the caramel coconut mixture onto the top of each fudge-striped cookie and gently spread it across the surface. Place the cookies on a parchment-lined baking sheet.
Melt the chocolate: Add the chocolate chips and coconut oil to a microwave-safe bowl and microwave in one-minute intervals, stirring between each, until the chocolate is smooth and fully melted.
Drizzle the chocolate: Transfer the melted chocolate to a piping bag or zip-top bag with the tip cut off and drizzle it over each cookie.
Let the cookies set: Allow the chocolate to harden before serving.