If you’re craving a dessert that feels like a warm hug on a plate, the Pineapple Upside Down Bread Pudding Recipe is an absolute must-try. Combining the rich, custardy texture of bread pudding with the tropical sweetness of caramelized pineapples and cherries, this delightful dish offers a perfect balance of comfort and brightness. Each bite reveals layers of buttery brown sugar caramel, tender brioche, and subtle cinnamon spice, making it a crave-worthy treat for any occasion. Whether you’re serving it for a family gathering or simply indulging in a weekend dessert, this Pineapple Upside Down Bread Pudding Recipe will quickly become one of your favorites.

Pineapple Upside Down Bread Pudding Recipe - Recipe Image

Ingredients You’ll Need

Simple, classic ingredients come together beautifully in this recipe, each playing a vital role in creating rich flavors, creamy textures, and that gorgeous golden finish. From the buttery brioche to the sweet pineapple and warm spices, every component is essential for achieving the perfect Pineapple Upside Down Bread Pudding Recipe.

  • 4 cups cubed brioche or challah bread: Day-old bread works best to soak up the custard without turning mushy.
  • 1/2 cup packed brown sugar: Adds deep caramel notes when melted with butter.
  • 1/4 cup unsalted butter: Provides richness and helps create that luscious caramel base.
  • 1 can (20 oz) pineapple slices, drained: Offers tropical sweetness and juicy bursts; reserve the juice for custard.
  • 8–10 maraschino cherries (optional): Adds color and a pop of contrasting sweetness in the pineapple centers.
  • 3 large eggs: The custard’s foundation, binding everything together with creaminess.
  • 1 1/2 cups whole milk: Creates a smooth, rich custard texture.
  • 1/2 cup heavy cream: Lends extra creaminess for a melt-in-your-mouth feel.
  • 1/4 cup granulated sugar: Sweetens the custard while balancing flavors.
  • 1 tsp vanilla extract: Adds warm, aromatic depth to the custard.
  • 1/2 tsp ground cinnamon: Brings cozy spice that complements the pineapple beautifully.
  • 1/4 tsp salt: Enhances all the flavors and balances sweetness.

How to Make Pineapple Upside Down Bread Pudding Recipe

Step 1: Prepare the Caramel Base

Start by preheating your oven to 350°F (175°C) and greasing your baking dish. Melt the butter and brown sugar over medium heat until bubbly and smooth, creating a rich caramel sauce. Pour this luscious caramel into the bottom of the dish, which will set the stage for the gorgeous pineapple topping and infuse the bread pudding with that irresistible buttery sweetness.

Step 2: Arrange Pineapple and Cherries

Place your carefully drained pineapple slices in a beautiful pattern over the caramel, and tuck maraschino cherries into the centers if you choose to use them. This step not only adds visual appeal but ensures every slice shines with bright tropical flavor after baking. The cherries also add a little burst of sweetness and a festive pop of color.

Step 3: Make the Custard Mixture

In a large bowl, whisk together the eggs, whole milk, heavy cream, granulated sugar, vanilla extract, cinnamon, salt, and 2 tablespoons of the reserved pineapple juice. This custard base contributes the creamy, tender texture that makes bread pudding so comforting, while the juice adds a hint of pineapple essence throughout the dish.

Step 4: Soak the Bread

Gently fold your cubed brioche into the custard, ensuring every piece gets coated lovingly. Let the mixture rest for 10 minutes so the bread absorbs all that flavorful custard magic. This soaking time is key to achieving the soft yet structured texture that defines the best bread puddings.

Step 5: Assemble and Bake

Spoon the soaked bread custard carefully over the pineapple and caramel layer, smoothing the top evenly. Bake for 40 to 45 minutes until the top is beautifully golden and the custard is set. A slight jiggle in the center is okay, but it should look firm and inviting. Let the pudding cool for 10 to 15 minutes before serving—it helps everything settle and makes flipping easier if you want to invert it.

How to Serve Pineapple Upside Down Bread Pudding Recipe

Pineapple Upside Down Bread Pudding Recipe - Recipe Image

Garnishes

To elevate this dessert, garnish with a dollop of freshly whipped cream or a generous scoop of creamy vanilla ice cream. A sprinkle of toasted coconut or chopped toasted pecans adds a delightful crunch and complements the tropical flavors beautifully. These simple touches make the Pineapple Upside Down Bread Pudding Recipe even more irresistible and festive.

Side Dishes

This pudding shines best on its own or paired with a light fruit salad or citrus sorbet to balance its richness. If serving for brunch, consider alongside a fresh green salad with a tangy vinaigrette to contrast the sweetness and add some fresh texture. The combination keeps the meal well-rounded and exciting.

Creative Ways to Present

Try serving the pudding in individual ramekins for a charming single-serve experience that feels extra special. Alternatively, flip the pudding onto a wooden board for a rustic, eye-catching presentation that encourages sharing. Drizzle extra caramel sauce or pineapple syrup over the top for a glossy finish that will make your guests’ eyes light up.

Make Ahead and Storage

Storing Leftovers

Simply cover your leftover Pineapple Upside Down Bread Pudding Recipe tightly with plastic wrap or store in an airtight container in the refrigerator. It will stay fresh for up to 3 days, making it perfect for enjoying a sweet treat the next day.

Freezing

If you want to keep it longer, this bread pudding freezes wonderfully. Wrap tightly in plastic wrap and aluminum foil, or place in a freezer-safe container, and freeze for up to 2 months. Thaw in the refrigerator overnight before reheating to preserve all the creamy texture and flavors.

Reheating

Reheat your pudding in the oven at 325°F (165°C) for about 15–20 minutes until warmed through. Cover loosely with foil to prevent overbrowning or drying out. You can also microwave individual servings for about 1–2 minutes, but oven reheating keeps the texture much closer to freshly baked.

FAQs

Can I use other types of bread?

Absolutely! While brioche or challah are ideal due to their richness and texture, you can substitute with white bread, French bread, or even croissants for an extra buttery flavor. Just make sure the bread is slightly stale or toasted to absorb the custard well.

Do I have to use maraschino cherries?

Not at all—maraschino cherries are optional and mainly for aesthetic and a pop of sweetness. You can omit them or try fresh cherries or even raspberries for a different twist.

Can I make this recipe dairy-free?

Yes! Swap the whole milk and heavy cream for your favorite plant-based alternatives like coconut milk or almond milk and use vegan butter or coconut oil in place of butter. The texture will vary slightly but remain deliciously satisfying.

What if I don’t have pineapple rings?

No worries! You can use pineapple tidbits instead. Just scatter them over the caramel layer and press slightly to secure before adding the bread pudding mixture. The flavor remains bright and tropical.

How long does the pudding take to set properly?

For the best texture, bake for 40 to 45 minutes until the top is golden and custard is set but still slightly jiggly in the center. Allow it to cool for 10–15 minutes before serving to help it firm up perfectly.

Final Thoughts

There is something incredibly comforting and joyful about the Pineapple Upside Down Bread Pudding Recipe that makes it a true crowd-pleaser. With a few simple ingredients and straightforward steps, you can create a dessert that tastes like a tropical vacation in every spoonful. So go ahead, try this recipe soon—you might just discover your new favorite way to enjoy bread pudding with a sunny, caramelized twist.

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Pineapple Upside Down Bread Pudding Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 4.1 from 204 reviews
  • Author: admin
  • Prep Time: 20 minutes
  • Cook Time: 45 minutes
  • Total Time: 1 hour 5 minutes
  • Yield: 6–8 servings
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Description

This Pineapple Upside Down Bread Pudding is a delightful twist on classic bread pudding featuring caramelized pineapple slices and cherries baked atop a rich custard-soaked brioche. The sweet and tangy pineapple melds beautifully with the creamy custard and buttery caramel base, making it a comforting tropical dessert perfect for any occasion.


Ingredients

Scale

Caramel and Fruit Layer

  • 1/2 cup packed brown sugar
  • 1/4 cup unsalted butter
  • 1 can (20 oz) pineapple slices, drained and juice reserved
  • 8–10 maraschino cherries (optional)

Bread Pudding

  • 4 cups cubed brioche or challah bread (day-old or lightly toasted)
  • 3 large eggs
  • 1 1/2 cups whole milk
  • 1/2 cup heavy cream
  • 1/4 cup granulated sugar
  • 1 tsp vanilla extract
  • 1/2 tsp ground cinnamon
  • 1/4 tsp salt
  • 2 tablespoons reserved pineapple juice (from the canned pineapple)


Instructions

  1. Preheat and prepare the baking dish: Set your oven to 350°F (175°C). Grease a 9-inch square or similarly sized baking dish to prevent sticking.
  2. Make the caramel layer: In a small saucepan over medium heat, melt together the unsalted butter and packed brown sugar, stirring occasionally until bubbly and smooth, about 2–3 minutes. Immediately pour this caramel mixture into the bottom of your prepared baking dish.
  3. Arrange the pineapple and cherries: Lay the drained pineapple slices evenly over the caramel layer in the baking dish. If using, place maraschino cherries in the center holes of the pineapple slices for a classic look.
  4. Prepare the custard mixture: In a large bowl, whisk together the eggs, whole milk, heavy cream, granulated sugar, vanilla extract, ground cinnamon, salt, and 2 tablespoons of the reserved pineapple juice until thoroughly combined.
  5. Soak the bread: Add the cubed brioche or challah bread to the custard mixture. Gently stir to coat all bread pieces evenly and let this mixture rest for 10 minutes so the bread absorbs the custard.
  6. Assemble the pudding: Carefully spoon the soaked bread mixture over the pineapple and caramel layer in the baking dish. Spread and smooth the top evenly.
  7. Bake: Place the baking dish in the oven and bake for 40 to 45 minutes, or until the top is golden brown and the custard has set firmly.
  8. Cool and serve: Remove from the oven and allow the pudding to cool for 10 to 15 minutes before serving. For an impressive presentation, invert the pudding onto a serving plate to reveal the pineapple topping, or serve directly from the dish.

Notes

  • Best served warm with whipped cream or vanilla ice cream for added indulgence.
  • You can substitute pineapple tidbits for slices if easier slicing is desired.
  • Day-old or lightly toasted bread works best to absorb the custard without becoming mushy.
  • Use a sturdy bread like brioche or challah for a rich texture.

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