Chocolate-Caramel Bread Pudding


6 ounce(s) Bittersweet Chocolate, chopped
2 cup(s) Heavy Cream
1 1/2 cup(s) Milk
2 tablespoon(s) Cocoa Powder
1/2 (vanilla bean) Seeds Scraped And Pod Reserved
1 large Egg
5 large Egg Yolks
1/4 teaspoon(s) Salt
1/2 cup(s) Sugar
7 cup(s) (13 ounces) Challah Bread, cut into 1-inch cubes
1 1/2 teaspoon(s) Unsalted Butter
6 ounce(s) Semisweet Chocolate Chips
4 ounce(s) Caramel Candy Chews, such as Werther's Original, halved


Make the pudding: 
Place the chocolate in a large bowl and set aside. Place the cream, milk, cocoa, and vanilla bean seeds and pod in a medium pot and bring to a simmer over medium heat. Remove from the heat, and strain into the bowl of chocolate. Gently stir to combine and set aside. Whisk the egg, yolks, salt, and sugar together in a medium bowl. Pour the cream mixture into the egg mixture in a slow, steady stream, whisking continuously until combined. Place the challah in a large bowl, pour the egg-and-cream mixture over the bread, and let sit, tossing occasionally, until the bread absorbs the liquid — about 30 minutes.

Bake the pudding: 
Heat the oven to 325 F. Lightly coat a 10-inch (1 quart) deep-dish pie pan with the butter. Gently mix chocolate chips and the soaked bread together. Spoon half of the pudding into the pie pan, sprinkle with half of the caramel candies, top with the remaining pudding and caramel. Tightly cover the pie pan with aluminum foil, fit it into a 10- by 15-inch roasting pan, and place them on the middle shelf of the oven. Fill the roasting pan with hot water until the level reaches halfway up the sides of the pie pan. Bake for 40 minutes, uncover, and continue to bake until the liquid has set and the caramel is melted — about 20 more minutes. Serve warm. Pudding can be stored covered tightly with plastic wrap and refrigerated for up to 3 days.

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