If you love classic comfort desserts with a tropical twist, this Pineapple Upside Down Bread Pudding Recipe is about to become your new favorite treat. It brings together the rich, custardy texture of bread pudding with the caramelized sweetness of pineapple rings and cherries, all baked to golden perfection. This delightful mash-up combines the nostalgic charm of a pineapple upside down cake with the indulgent warmth of bread pudding, making every bite a comforting, fruity hug. Whether you’re serving it for a special occasion or a cozy gathering, this recipe will brighten up your dessert table and leave everyone asking for seconds.

Pineapple Upside Down Bread Pudding Recipe - Recipe Image

Ingredients You’ll Need

The beauty of this Pineapple Upside Down Bread Pudding Recipe lies in its simple, approachable ingredients that work in harmony to create a stunning mix of flavors and textures. Each component adds a unique touch — from the buttery base that caramelizes the sugar to the custard that soaks into the bread, creating a luscious bite every time.

4 tablespoons unsalted butter (melted): Creates a rich, golden base that blends with the brown sugar for caramelization.
½ cup brown sugar (packed): Adds deep, molasses-like sweetness and helps form the signature topping glaze.
1 can (20 oz) pineapple slices in juice (drained, juice reserved): The star fruit that infuses juicy, tropical flavor right at the bottom layer.
8 maraschino cherries: Provide pops of bright color and a sweet contrast inside each pineapple ring.
6 cups day-old brioche or challah bread (cut into 1-inch cubes): Stale bread soaks in custard perfectly for that soft, spongy texture.
4 large eggs: The binding agents that create the custard’s creamy structure.
1 ½ cups whole milk: Offers creaminess and moisture within the custard base.
½ cup heavy cream: Adds richness and velvety texture to the custard mixture.
½ cup granulated sugar: Sweetens the custard while balancing the brown sugar topping.
1 teaspoon vanilla extract: Elevates the flavor with warm, fragrant notes.
½ teaspoon cinnamon: Lends a hint of spice that pairs beautifully with the tropical fruit.
¼ teaspoon salt: Enhances all the flavors, bringing balance to the sweetness.

How to Make Pineapple Upside Down Bread Pudding Recipe

Step 1: Prepare the Caramelized Pineapple Base

Start by preheating your oven to 350°F (175°C) and greasing a 9×9-inch baking dish. Pour the melted butter evenly over the bottom and swirl it around so the entire base is coated. Sprinkle the packed brown sugar on top, creating the sugary layer that will transform into caramel during baking. Arrange the pineapple slices neatly over the brown sugar and place one maraschino cherry right in the center of each pineapple ring. This creates a visually stunning upside-down effect when you flip the pudding later.

Step 2: Make the Custard Mixture

In a large bowl, whisk together the eggs, whole milk, heavy cream, granulated sugar, vanilla extract, cinnamon, salt, and a quarter cup of the reserved pineapple juice. This delicious custard will soak into the bread to create that soft, custardy texture that defines the dish. The pineapple juice adds an extra layer of tropical brightness to the mixture that pairs perfectly with the baked fruit base.

Step 3: Soak the Bread

Gently stir the cubed brioche or challah into the custard mixture, making sure every piece is fully coated. Let it sit for about 10 minutes, allowing the bread to absorb the flavorful custard. This soaking step is essential for the soft, pudding-like texture you’ll crave.

Step 4: Assemble and Bake

Spoon the soaked bread mixture carefully over the pineapple and cherry layer in your baking dish. Press down gently with the back of the spoon to compact the bread, helping it bake evenly. Slide it into the oven to bake for 45 to 50 minutes or until the pudding is golden on top and set in the center. Once done, give it a cool-down period of 10 to 15 minutes before you invert it onto a serving platter to reveal that gorgeous pineapple and cherry topping.

How to Serve Pineapple Upside Down Bread Pudding Recipe

Garnishes

Finish your presentation with a sprinkle of toasted coconut flakes or a dusting of powdered sugar for an elegant touch. Fresh mint leaves make a lovely visual and fragrant accompaniment, while a drizzle of warm caramel sauce amps up the indulgence factor to delight any sweet tooth.

Side Dishes

This dessert pairs wonderfully with a scoop of vanilla ice cream or a dollop of lightly whipped cream for contrasting coolness and creaminess. If you want to add a bit of texture, a handful of crushed macadamia nuts or candied pecans on the side introduce a satisfying crunch alongside the pudding’s softness.

Creative Ways to Present

Serve individual portions in ramekins for an intimate dessert experience that looks professional and charming. You can also layer the pudding in clear glasses with extra pineapple chunks and a drizzle of coconut cream, turning the simple pudding into a tropical parfait. For a brunch twist, pair it with a citrusy fruit salad and a cup of freshly brewed coffee or tea.

Make Ahead and Storage

Storing Leftovers

If you have any leftovers (which you might, but probably won’t), cover them tightly in plastic wrap or transfer to an airtight container. Store in the refrigerator for up to 3 days to keep the pudding moist and flavorful without drying out.

Freezing

You can freeze this bread pudding by wrapping it tightly in foil and then placing it in a freezer-safe bag or container. It keeps well for up to 2 months. When ready to enjoy, thaw in the refrigerator overnight before reheating.

Reheating

Reheat leftovers by warming them gently in the oven at 325°F (165°C) for about 15 minutes or until heated through. Alternatively, microwave individual servings for a quick option, but keep the time short to avoid drying out the pudding.

FAQs

Can I use bread other than brioche or challah for this recipe?

Absolutely! While brioche and challah are ideal for their rich texture and flavor, you can substitute with other sturdy breads like French bread or even Texas toast. Just be sure it’s day-old or slightly stale to soak up the custard properly.

Is it possible to make this dessert vegan or dairy-free?

Yes, you can adapt this Pineapple Upside Down Bread Pudding Recipe by using plant-based milks like coconut or almond milk, vegan butter, and egg replacers. The texture might be a bit different, but you’ll still get that lovely tropical flavor.

Can I add other fruits to this pudding?

Definitely! While pineapple is the star, things like diced mango, papaya, or even sliced bananas can add an interesting dimension. Just make sure to adjust the sugar slightly since some fruits are sweeter than others.

Why do I need to reserve the pineapple juice?

The reserved pineapple juice adds extra flavor and moisture to the custard, enhancing the tropical twist and balancing the sweetness with a subtle tang. Don’t skip it — it really makes a difference!

What is the best way to ensure the pudding is cooked through?

Look for a golden top and a custard that’s set but still slightly jiggly in the center when baked. You can insert a toothpick into the middle — it should come out mostly clean with a few moist crumbs but no wet batter.

Final Thoughts

This Pineapple Upside Down Bread Pudding Recipe is one of those magical dishes that feels like a hug from the inside out. It’s cozy yet bright, familiar yet new — truly a dessert that brings joy at the very first bite. I can’t wait for you to try it and see just how effortlessly it can become a beloved classic in your kitchen too.