
Pineapple Upside Down Bread Pudding with King’s Hawaiian Rolls
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Turning pineapple upside down cake into a bread pudding? That’s already a win. But swap in sweet, pillowy King’s Hawaiian rolls for plain bread, and you’ve got something extra special. This dessert combines the gooey caramelized topping of the classic cake with the custardy comfort of a rich bread pudding. It’s buttery, sweet, tropical, and nostalgic all at once. Whether you’re making it for a holiday dessert table or just craving something cozy, this one-pan bake brings bold flavor without the fuss. And if you’re a fan of King’s Hawaiian rolls, this might become your new favorite dessert.
Pineapple Upside Down Bread Pudding: A Hawaiian Roll Makeover
Rated 5.0 stars by 1 users
Category
Dessert
Cuisine
American
Author:
Glenn Connaughton
Servings
10
Prep Time
20 minutes
Cook Time
50 minutes
Calories
390
This recipe takes the familiar comfort of pineapple upside down cake and transforms it into a rich, decadent bread pudding. Instead of white bread, we use King’s Hawaiian rolls for a soft, sweet base that soaks up the vanilla custard like a dream. Brown sugar and butter melt together with pineapple and cherries for that signature caramelized topping. Once baked, the pudding flips beautifully and delivers that golden, gooey crown. Drying the rolls beforehand helps keep the texture custardy, not mushy. Serve warm with whipped cream or a scoop of ice cream for a dessert that’s pure comfort and a little bit of tropical sunshine.

Ingredients
Topping
- 1/2 cup salted butter (1 stick)
- 1 cup packed brown sugar
- 1 can (20 ounces) pineapple rings in juice, drained and juice reserved
- 10 maraschino cherries
Custard + Bread:
- 6 King’s Hawaiian rolls (about 10 ounces), cut into 1-inch cubes
- 3 large eggs
- 1 cup milk
- 1 cup heavy cream
- 1/3 cup white granulated sugar
- 1 teaspoon vanilla extract
Sauce
- 6 Tablespoons (85 g) unsalted butter, cut into pieces
- 4 tablespoons Hawaiian Gold Rum
-
2 Tablespoons heavy cream
- ¾ cup (150 g) packed brown sugar
Directions
Prep the Bread: Cut the King’s Hawaiian rolls into 1-inch cubes. Spread the cubes on a baking sheet and let them sit out overnight to dry. If you're short on time, bake them at 250 degrees Fahrenheit for 15 to 20 minutes, stirring halfway through, until dry but not toasted. Let cool.
Preheat the Oven: Preheat your oven to 350 degrees Fahrenheit. Grease a 9x9-inch baking dish generously with butter or nonstick spray.
Make the Topping: In a small saucepan, melt the butter over medium heat. Stir in the brown sugar until smooth and bubbling. Pour the mixture evenly into the prepared pan.
Add the Fruit: Arrange the pineapple rings over the brown sugar topping. Place a maraschino cherry in the center of each ring.
Make the Custard: In a large bowl, whisk together the eggs, milk, cream, sugar, vanilla extract, and 1/4 cup of the reserved pineapple juice.
Combine Bread & Custard: Place the dried bread cubes in a large bowl. Pour the custard over the bread and gently stir. Let soak for 10 minutes so the bread can absorb the liquid.
Assemble & Bake: Spoon the soaked bread mixture evenly over the pineapple topping in the baking dish. Bake uncovered for 45 to 50 minutes, until golden brown and set in the center.
Rest & Flip: Let rest for 10 minutes. Run a knife around the edges of the pan and carefully invert onto a serving platter. Spoon any stuck topping back over the pudding.
Optional Rum Sauce Instructions
- While the bread pudding bakes, make the rum sauce. Brown the butter over medium-low heat. Stir occasionally and scrape the bottom of the pan to prevent burning. The butter will get foamy.
- Once the butter has a nutty aroma, add the brown sugar, rum and heavy cream. Whisk until sugar is dissolved. Remove from heat to cool slightly.
- Pour sauce over bread pudding and serve warm.
Recipe Note
Drying out the rolls first makes all the difference—giving you a pudding that holds together with the perfect custardy texture. Serve it up warm with a scoop of vanilla ice cream or a dollop of whipped cream and let that buttery pineapple topping shine. For more sweet creations and savory rubs, explore everything we offer at #revolutionbbq.
Nutrition information is automatically calculated, and should only be used as an approximation
Serving Size
1 Serving (210 grams)
Calories 390,
Fat
20 grams,
Polyunsaturated Fat
1.8 milligrams,
Monounsaturated Fat
5.5 milligrams,
Carbs
47 grams,
Protein
5 grams,
Potassium
165 milligrams,
Fiber
1 grams,
Sodium
240 milligrams,
Sugar
32 grams,
Iron
1.4 milligrams