Preheat the oven to 350 degrees F (180 degrees C).
Add the Challah Bread (1 loaf) on a baking sheet and place in oven for 10 minutes or until dried out.
Reserve 1 cup of bread cubes for topping and transfer the rest to a buttered baking dish. Toss in Chocolate Chips (1/4 cup).
In a large bowl combine the Milk (2 1/2 cup), Heavy Cream (2 1/2 cup), and Egg (9) until mixed.
Add the Granulated Sugar (3/4 cup), Kosher Salt (3/4 teaspoon), Vanilla Extract (3 teaspoon), and Unsweetened Cocoa Powder (3 tablespoon). Pour over the bread and allow to sit for 30 minutes, pressing down with a spatula every 10 minutes.
Reduce the oven to 325 degrees F (160 degrees C). Add the reserved bread cubes and press into custard. Sprinkle over remaining chocolate chips. Bake 50 minutes or until custard has set. As it bakes, prepare the chocolate sauce.
Melt the Granulated Sugar (1/2 cup) with the Heavy Cream (1/2 cup) in a small sauce pan. Stir in the Butter (2 tablespoon) and Chocolate Chips (1/4 cup) until melted. Stir in the Chocolate Liqueur (2 tablespoon) and allow to heat for 3 minutes.
Top pudding with chocolate sauce and enjoy warm.