Preheat your oven to 350°F and lightly grease a 9×13-inch baking dish. This dessert bakes best in a glass or ceramic dish because it helps the caramel stay soft and gooey while the top becomes rich and fudgy.

In a large mixing bowl, combine the chocolate cake mix, milk, melted butter, and vanilla extract until just combined. The batter will be thick, which helps create those rich layered textures once baked.

Spread half of the chocolate batter evenly into the prepared baking dish. Drizzle half of the caramel sauce and sweetened condensed milk over the batter, then sprinkle with half of the chocolate chips and caramel bits.

Carefully spoon the remaining cake batter over the top. It does not need to completely cover every area because the cake spreads while baking and creates a rustic, gooey texture.

Finish by drizzling the remaining caramel sauce over the top and adding the rest of the chocolate chips and caramel pieces. The extra caramel melts into the cake and creates rich pockets of sauce throughout the dessert.

Bake for 38 to 45 minutes, or until the edges are set and the center is still slightly soft. The middle should look gooey but not completely liquid. Avoid overbaking because the cake continues to set as it cools.

Let the cake rest for about 15 minutes before serving. This gives the caramel time to thicken slightly while still keeping the dessert warm and fudgy.

Serve warm with vanilla ice cream or whipped cream for the perfect chocolate caramel dessert experience.