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 9
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.