Cinnamon Roll Bread Pudding

Step 1
Preheat oven to 400 degrees F (200 degrees C). Grease a baking sheet with cooking spray; place rolls on top, 2 inches apart. Reserve icing.

Step 2
Bake in the preheated oven until golden brown, 8 to 10 minutes. Cool on the baking sheet for 5 minutes. Transfer to a wire rack. Let stand, uncovered, until stale, 8 hours to overnight.

Step 3
Preheat oven to 300 degrees F (150 degrees C). Grease a 2-quart baking dish with cooking spray.

Step 4
Cut stale cinnamon rolls into 1/2-inch cubes. Whisk heavy cream, brown sugar, 2/3 cup milk, egg yolks, vanilla extract, 3/4 teaspoon cinnamon, and salt in a large bowl. Toss in cinnamon roll cubes until evenly coated. Let stand, tossing occasionally, until cubes being to absorb cream mixture, about 30 minutes.

Step 5
Pour mixture into the prepared baking dish. Cover with aluminum foil.

Step 6
Bake in the preheated oven until almost set, about 45 minutes.

Step 7
Mix 2 tablespoons white sugar and 1/4 teaspoon cinnamon together in a small bowl. Rub in 1/4 cup butter with your fingers until topping is in pea-sized crumbs.

Step 8
Uncover baking dish and sprinkle topping on top. Continue baking, uncovered, until custard is set, 20 to 25 minutes. Increase oven temperature to 450 degrees F (230 degrees C). Bake until bread pudding forms a golden crust, about 2 minutes more.

Step 9
Warm reserved icing in a small microwave-safe bowl, about 15 seconds. Drizzle hot icing carefully over bread pudding. Cool on a wire rack, about 30 minutes.

Step 10
Melt 2 tablespoons butter in a saucepan over medium heat. Mix 1/2 cup sugar and cornstarch together; stir into the melted butter. Pour in milk and bourbon, stirring frequently until mixture begins to boil. Cook, stirring constantly, until thickened, about 5 minutes. Remove from heat.

Step 11
Spoon cooled bread pudding onto serving plates. Drizzle warm sauce on top.