Preheat the oven to 350 degrees F. Generously spray a 9 by 13-inch baking dish with cooking spray.
In a large bowl, beat the brownie mix with the eggs, chocolate milk, and oil until just combined. Using a spatula, fold in 1/2 cup chocolate chips. Spread into the prepared baking dish and bake until center is barely set, 25 to 30 minutes. Remove from the oven and cool completely.
Heat the cream in a small saucepan over medium low heat. Stir in the caramels until completely melted and incorporated into the cream. Remove from the heat and stir in the coconut. Spread in an even layer over the cooled brownies.
Melt the remaining chocolate chips in the microwave at 15 second intervals, stirring between intervals. Drizzle the chocolate in a criss-cross pattern over the coconut topping. Place in the refrigerator for at least 30 minutes to set before slicing into bars.