Preheat the oven to 350°F (175°C) and bake the brownie mix according to package instructions, about 25-30 minutes. Once baked, cool completely in the pan before crumbling.

In a mixing bowl, cream together the softened butter, brown sugar, and granulated sugar until light and fluffy, about 2-3 minutes. Gradually add the flour and vanilla, mixing until combined. Adjust with milk if needed. Fold in chocolate chips and cherries.

Take a handful of crumbled brownies and flatten them into a disc. Place cookie dough in the center and fold the edges around the filling. Roll into a ball and repeat until all ingredients are used.

Melt the chocolate chips in a microwave-safe bowl. Dip each brownie bomb in the chocolate until coated, then let excess chocolate drip off. Place on a parchment-lined tray.

Press a maraschino cherry on top of each coated brownie bomb while the chocolate is still wet. Allow to set completely before serving.