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Pineapple Upside Down Bread Pudding Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 3.9 from 76 reviews
  • Author: Kimberly
  • Prep Time: 20 minutes
  • Cook Time: 50 minutes
  • Total Time: 1 hour 10 minutes
  • Yield: 9 servings
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Description

This Pineapple Upside Down Bread Pudding is a luscious tropical dessert featuring caramelized pineapple rings and maraschino cherries atop a rich custard-soaked brioche bread base. Baked to golden perfection, it offers a comforting blend of fruity sweetness and creamy texture, perfect for serving warm or at room temperature.


Ingredients

Caramelized Topping

  • 4 tablespoons unsalted butter (melted)
  • ½ cup brown sugar (packed)
  • 1 can (20 oz) pineapple slices in juice (drained and juice reserved)
  • 8 maraschino cherries

Bread Pudding Custard

  • 6 cups day-old brioche or challah bread (cut into 1-inch cubes)
  • 4 large eggs
  • 1 ½ cups whole milk
  • ½ cup heavy cream
  • ½ cup granulated sugar
  • 1 teaspoon vanilla extract
  • ½ teaspoon cinnamon
  • ¼ teaspoon salt
  • ¼ cup reserved pineapple juice


Instructions

  1. Prepare the Baking Dish: Preheat your oven to 350°F (175°C). Grease a 9×9-inch baking dish to ensure the bread pudding doesn’t stick.
  2. Create the Caramelized Base: Pour the melted butter evenly into the bottom of the baking dish and swirl it to coat. Sprinkle the packed brown sugar over the butter evenly. Arrange the drained pineapple slices atop the sugar layer and place a maraschino cherry in the center of each pineapple ring, creating an appealing pattern.
  3. Make the Custard Mixture: In a large bowl, whisk together the eggs, whole milk, heavy cream, granulated sugar, vanilla extract, cinnamon, salt, and ¼ cup of the reserved pineapple juice until smooth and well combined.
  4. Soak the Bread: Add the cubed brioche or challah bread into the custard mixture, stirring gently to fully coat each piece. Allow the bread to soak for about 10 minutes so it absorbs the custard flavors thoroughly.
  5. Assemble and Bake: Carefully spoon the soaked bread mixture over the pineapple and sugar layer in the baking dish. Press down lightly to compact the bread evenly. Place the dish in the preheated oven and bake for 45 to 50 minutes, or until the pudding is golden brown and set in the center.
  6. Cool and Serve: Remove the bread pudding from the oven and let it cool for 10–15 minutes. Invert the dish onto a serving platter to reveal the caramelized pineapple topping. Serve warm or at room temperature for a delightful dessert experience.

Notes

  • Brioche or challah bread works best for a soft, rich texture in the pudding.
  • For added flavor and texture, consider mixing in shredded coconut or chopped nuts.
  • Leftover bread pudding can be stored in the refrigerator and reheated in the oven or microwave before serving.