Preheat oven to 350 degrees and generously grease an 8" pie dish.
In a small mixing bowl, combine ? cup sugar, milk, oil, and vanilla. Whisk well and set aside.
In a large mixing bowl, combine flour, 6 tablespoons cocoa, baking soda, and salt; whisk well. Pour wet ingredients into dry ingredients and mix until well combined; fold in chocolate chips. Batter should be smooth and thick.
Evenly spoon batter into greased baking dish. Place dish on a baking sheet in case of spillover.
In a small bowl, combine remaining ? cup sugar and 2 tablespoons cocoa; whisk well. Evenly sprinkle this mixture on top of the batter in dish. Pour red wine over the prepared dish. Do not mix!
Bake for 35-40 minutes. Pudding should be bubbling and slightly firm to the touch. Allow to cool for 15-20 minutes before diving in. Pair with a glass of red wine, a cold glass of allergy friendly milk, or a strong cup of coffee.