Pineapple Upside-Down Bread Pudding

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Pineapple Upside-Down Bread Pudding contains all the wonderful fruity flavors of the traditional upside-down cake but in bread pudding form! This bread pudding cake has a caramelized top layer with a super moist, buttery, melt-in-your-mouth interior.

Pineapple Upside Down Bread Pudding

 Pineapple Upside-down Cake makes me think of Spring. I don’t know, maybe it’s the pineapple maraschino combo.

I always have that fruit combo in my favorite cocktail!

And I have this cocktail on the beach.

I go to the beach in the Spring and Summer.

So hot weather equals pineapple maraschino combo equals Pineapple Upside-Down Cake.

See how that works?

See how my brain works?

Beware, it’s a pretty scary place!

 Pineapple Upside Down Bread Pudding

 I’m so excited to share this Pineapple Upside-Down Bread Pudding with you today. I normally am scheduled out on the blog about three weeks ahead. I’m so excited about sharing this that I rearranged to post it earlier!

I had a brainstorm (my brain was working overtime!). I had old bread I needed to use, but I wanted pineapple something! So this fabulously tasty Pineapple Upside-down Bread Pudding was born!

Pineapple Upside Down Bread Pudding

The butter and brown sugar cook and caramelize making a crispy outside. The pineapple and cherries almost turn into candy during the process. Have you ever had candied orange or other fruit? That’s what I’m talking about! Even though the outside is crispy and the fruit is caramelized, the center of this bread pudding is smooth and creamy.

This bread pudding has a slightly sweet glaze that the brown sugar and butter create but it’s not an overly sweet or over rich dessert. The cherries offer a tart tangy-ness which is the real kicker. The combo of the buttery brown sugar and cherry juice seeping into the cake will be the reason you can stop eating this dessert! It’s the reason I had to give it to a friend so I wouldn’t eat the entire cake!

Pineapple UPside Down Bread PUdding

I made this bread pudding twice in order to perfect it before sharing. I added ground cinnamon the second time and it made a huge difference. The cinnamon gave a nice back note of flavor and paired well with the pineapple.

Are you familiar with making bread pudding? It’s an economical dessert to make. That’s why a lot of restaurants have it on the menu. It’s a way for restaurants to use their old bread and not have that waste. Actually, it’s preferable to use old bread rather than fresh bread. Not old like it has mold specks on it, but old as in slightly dried out. When bread is dry it will absorb the custard better. I usually get french bread that has been discounted at the grocery store for my bread pudding. I save about 50% buying old bread. It adds up.

Pineapple Upside Bread Pudding

This cake is best fresh out of the oven maybe even with vanilla ice cream. I enjoyed it without ice cream and it was fantastic. If it isn’t devoured immediately you want to store this moist cake in the refrigerator. Of course, you could eat it cold, but I recommend heating the leftovers up one slice at a time in the oven or toaster oven. This will crisp up the outside again. Although popping it in the microwave is super easy and quick, to me it changes the texture and for once, I’d rather be patient and heat it in the oven.

Pineapple Upside Down Bread Pudding slice

PIneapple Upside Down Bread Pudding

Pineapple Upside-Down Bread Pudding

This Bread Pudding contains all the wonderful fruity flavors of the traditional Pineapple Upside Downcake, but in bread pudding form! It has a caramelized top layer with a super moist, buttery, melt-in-your-mouth interior.
Author: Paula
5 from 6 votes
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Prep Time: 30 minutes
Cook Time: 45 minutes
Total Time: 1 hour 15 minutes
Servings: 14 servings
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  • 1 cup brown sugar packed
  • 1/2 cup butter I don't recommend substituing margarine or coconut oil in this recipe
  • 1 pound French bread you will get about 10 cups of bread cubes once they're cut
  • 12 ounces evaporated milk
  • 14 ounces sweetened condensed milk
  • 3 large eggs at room temperature
  • 1 tablespoon vanilla yes, tablespoon
  • 1/2 teaspoon ground cinnamon
  • 1 cup sugar
  • 1/8 teaspoon salt
  • 7 slices pineapple
  • 7 maraschino cherries


  • Mix evaporated milk and sweetened condensed milk together.
  • Beat eggs, add to milk and stir.
  • Add vanilla, sugar, cinnamon, and salt to milk mixture and stir.
  • Pour milk mixture over cubed bread in a large bowl.
  • Allow to sit 10 minutes.
  • Wrap heavy aluminum foil around bottom of 10 inch spring-form pan. Heat oven to 375 degrees and melt butter in oven in the spring form pan. Remove from oven and sprinkle brown sugar evenly over butter.
  • Drain pineapples and cherries. Place one slice of pineapple in center of pan over butter and brown sugar. Place other pineapple rings around the center one. Place a cherry inside each pineapple ring. (You can fill every gap with a cherry if you wish.)
  • Carefully, spoon breading mixture over pineapple slices. Press firmly down.
  • Bake in a 375° oven for 40 to 45 minutes. Center will be set and bread golden brown.
  • Allow cake to cool 10 minutes in pan before inverting on a serving platter.


  • You can substitute 1%, 2% or whole milk for evaporated milk, it will be slightly less creamy.
  • I used a 10 inch springform pan for this recipe. You could also use a cast-iron skillet.
  • Day old bread is good for this recipe as it will absorb more of the custard. If you don't have old bread, cut the bread into cubes and dry out in a 200 degree oven for 10 minutes.


Calories: 436kcal | Carbohydrates: 73g | Protein: 10g | Fat: 13g | Saturated Fat: 7g | Cholesterol: 79mg | Sodium: 329mg | Potassium: 304mg | Fiber: 1g | Sugar: 53g | Vitamin A: 426IU | Vitamin C: 21mg | Calcium: 187mg | Iron: 2mg
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  1. 5 stars
    This is so clever, reminds me of my grandma’s cake but in bread pudding form!! We loved it . . and I’m going to have to start looking for the discounted bread as you mentioned. It seems so wastful (and time consuming) to pay full price for a loaf and then wait around for it to get stale — haha

  2. 5 stars
    I absolutely loved the refreshing fruity flavor of this bread pudding! Such a nice switch up from the heavy ones I’m used to.

  3. 5 stars
    My nana used to make bread pudding and this recipe brought me back to childhood. I LOVE the pineapple and cherry combination in this recipe. Absolutely delicious!

  4. This is such a clever way to elevate a day old bread into another dessert. I just made this and added chopped pineapple bits in between layers and added big chunks of pineapple on top and a dash of cinnamon and it tasted soo good! Thanks for sharing this simple and easy to make recipe! my husband loved it!

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Your email address will not be published. Have you tried this recipe? Consider giving it 5 stars!