Spray a 9x13 baking dish with cooking spray. Tear your bread into 1-inch pieces and place evenly in dish.
In a medium bowl, add whipping cream, milk, sugar, 1 teaspoon vanilla, 1 teaspoon cinnamon and eggs. Whip until combined. Pour over the bread and let rest for 5 minutes.
Spread pie mixture evenly over the bread and bake uncovered for 50 minutes. Remove from oven and allow to cool while you make icing. Combine the confectioner sugar and milk. Add the remaining cinnamon and vanilla and stir to combine. Drizzle over the warm bread pudding and serve.