Preheat the oven to 350°F. Grease an 8x8-inch baking dish.
Place the torn biscuits in the prepared baking dish. Sprinkle the chocolate chips evenly throughout the biscuit pieces.5 cups leftover fresh milled flour biscuits (448 g),1/2 cup semisweet chocolate chips.
In a large bowl, whisk together the milk, eggs, granulated sugar, cinnamon, vanilla, salt, and melted butter until well combined. 2 1/4 cups whole milk,4 large eggs,3/4 cup granulated sugar,2 teaspoons ground cinnamon,2 teaspoons vanilla extract,1/4 teaspoon salt,2 tablespoons butter.
Pour the custard evenly over the biscuits. Gently press the biscuit pieces into the custard so they are evenly moistened.
Let the bread pudding sit for 12 to 15 minutes to allow the biscuits to absorb the custard. The biscuits should be thoroughly moistened with some custard still visible between the pieces, but they should not be floating in liquid.
Bake uncovered for 43 to 48 minutes, or until the center is set but still soft. If the top begins to brown too quickly, loosely tent with aluminum foil for the remaining baking time. The bread pudding will continue to set as it cools.
While the bread pudding is baking, add the brown sugar and butter to a small saucepan. Cook over medium-low heat, stirring until the butter is melted and the mixture is smooth. 1/2 cup packed brown sugar,4 tablespoons butter.
Slowly stir in the heavy cream. Bring to a gentle simmer and cook for 2 to 3 minutes, stirring frequently, until the sauce is smooth and slightly thickened. 1/2 cup heavy cream.
Remove the caramel sauce from the heat and stir in the vanilla. 1 teaspoon vanilla extract.
Let the bread pudding rest for 10 to 15 minutes before serving. Spoon the warm caramel sauce over each serving.
Notes
Pro Tip: Don't skip the 12 to 15 minute soak before baking. This gives the biscuits time to absorb the custard so they bake up incredibly soft and tender.