Melt the chocolate chips until they are smooth.
Brush the entire surface of the cookie cake with the melted chocolate and reserve any leftover for drizzling. Allow the chocolate on the cookie cake to harden (at room temp or in the fridge) then invert the cookie so that the chocolate portion is on the bottom.
Toast the coconut by spreading it onto a baking sheet and baking it for 5 to 7 minutes, stirring frequently, as coconut will burn quickly. Add the toasted coconut to a large bowl.
In a medium saucepan set over medium heat, cook the caramels and milk until they are melted and smooth, stirring as needed. Brush the top of the cookie (the non-chocolate side) with a portion of the melted caramel, then pour the remainder of the caramel over the toasted coconut, stirring until the coconut is well coated. Working quickly, press the caramel-coated coconut on top of the cookie cake.
Drizzle the cookie cake with the remaining melted chocolate and let it sit until the chocolate has fully hardened.
Slice and serve.