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Pineapple Upside Down Cake is an old-fashioned recipe that is absolutely delicious with a buttery, moist crumb and sweetly caramelized fruit on top that makes for a beautiful presentation without a need for additional decoration! Serve it warm or room temperature with whipped cream or a small scoop of vanilla ice cream for a special treat!

Pineapple is such a delicious fruit but it doesn’t get the attention it deserves when it comes to baking! Some of our other favorite pineapple recipes are Tropical Pineapple Sponge Cake (a vintage favorite that is baked in a tube pan like an angel food cake) and Pineapple Casserole (a southern favorite that can be either a side dish or a dessert!).

Pineapple Upside Down Cake From Scratch

I feel like this vintage classic has been experiencing a resurgence in popularity in recent years. It’s an old-fashioned recipe that is simple to make despite it’s impressive appearance. The top (or bottom?) is decorated with gorgeously caramelized slices of pineapple and bejeweled with maraschino cherries, while the cake itself is a soft, tender yellow cake infused with pineapple juice for added flavor and moisture.

It’s a fun bake with the suspense of the topping being cooked on the bottom of the pan, then flipping the whole thing over to present it at the last minute. Will it turn out? Will it be as beautiful and yummy as you dream? The answer to both questions is a most definite “YES!”

By the way, I’m kicking off Spring Sweets Week with this pineapple upside down cake. Each of the bloggers participating is sharing new recipes each day that are perfect for spring celebrations! Keep scrolling past the recipe for all the details, links to their recipes, and giveaway information!

I hadn’t actually had pineapple upside down cake in YEARS until I recently watched an episode of the Great British Bake Off where they made Paul Hollywood’s version in individual ramekins. Which you could certainly do with this recipe, although I love the classic styling and family approach of one cake sliced into wedges.

Everybody in my family loved this dessert, which is a testament to its deliciousness since MY Paul (not Mr. Hollywood) often turns up his nose at desserts that don’t have chocolate in them. It took all my will-power not to sliver off a small piece of the leftover cake every time I walked past it in the kitchen.

What You’ll Need

No big surprises here! The ingredients in pineapple upside down cake are pantry staples that most home bakers will already be familiar with.

  • Pineapple Slices: I don’t recommend using fresh pineapple for this recipe. Not only are pineapple rings (the kind that come already sliced in a can) easier, but they give you that traditional, classic look without going to the trouble of cutting up the pineapple yourself into rings. Also, canned pineapple has been processed a bit so once it’s drained from the juice it is packed in, it will release much less liquid than if you were to use fresh pineapple.
  • Maraschino Cherries: These preserved, sweetened cherries are so yummy and add a beautiful ruby jeweled pop of color to our pineapple upside down cake. We always have a jar or two in the pantry for sundaes, Shirley Temples, or making a cherry chip cake.
  • Brown Sugar: You can use either light or dark brown sugar in this recipe. When measuring brown sugar, you should really pack it in to the measuring cup to the point that it holds its shape when you dump it out.
  • Granulated Sugar: The combination of brown sugar and granulated sugar gives the best flavor in what is essentially just a half-batch of a yellow cake poured over the pineapple upside down cake topping.
  • Butter: I use salted butter in almost all of my baking. You will use part of the butter in the recipe to create the topping, and the rest will be added to the cake batter.
  • Flour: I prefer cake flour for this particular cake because its low gluten content results in a lighter crumb that is super soft and fluffy, but the recipe will work just as well with all-purpose flour if that’s all that you have on hand.
  • Egg: One egg is enough to help bind the cake batter and create the fluffy texture of a soft, moist cake.
  • Vanilla Extract: I have been using my homemade vanilla extract for a while now and love it!
  • Sour Cream: Adding sour cream to cakes is a common trick that helps keep the cake nice and moist. It’s one of my go-to cake ingredients when I want moisture but not necessarily the tang that you get from using buttermilk. Greek yogurt makes a good substitute if you don’t have sour cream.
  • Milk: It’s a fairly small amount, but adds enough liquid to bring the batter together, especially since it’s already a thick batter. Whole milk is my choice when baking, but you can get away with low-fat milk here.
  • Pineapple Juice: When you drain the pineapple slices, be sure to save some of the juice to help flavor the cake batter. If you forget, it’s okay: just replace the pineapple juice with the same amount of additional milk. But it does add a nice subtle flavor to the batter.
  • Baking Powder: This ingredient provides lift for a light, fluffy cake.
  • Salt: Don’t forget and leave the salt out of your baked goods! It’s crucial to bringing out all of the other flavors so the cake isn’t bland.

How to Make Pineapple Upside Down Cake

  1. A little prep first: You know the drill — Preheat the oven to 350 degrees F and spray a 9-inch pan with baking spray. Go ahead and drain the pineapple (don’t throw out the juice!) and lay the pineapple rings and cherries on some paper towels. Blot the tops with more paper towels to get rid of as much moisture as you can.
  1. Make the topping: Heat the butter in the microwave in a small bowl until melted (or do this in a saucepan on the stove), then add the brown sugar and spread this mixture in the bottom of the cake pan. I find it’s easiest to do this with a rubber spatula or just using my hands to pat it into a thin, even layer.
  2. Arrange the fruit: Seven pineapple rings fit perfectly in the bottom of a 9-inch round pan. Slice the remaining rings in half and set them around the edges of the pan. Put a maraschino cherry in the hole of each pineapple ring and the spaces around the edges.
  1. Make the cake batter: This is a simple, standard cake batter. First cream the butter and sugars for 2-3 minutes until light. Add in the egg, sour cream, milk, pineapple juice, and vanilla extract, then mix again, making sure to scrape the bowl so it all gets mixed together. It’s totally normal for the batter to look “broken” or curdled at this point. Add the flour, baking powder, and salt, then mix again until combined and you will end up with a lovely, thick batter.
  1. Pour the batter over the filling: You will need to use a spatula or knife to spread the batter out a bit since it’s fairly thick. Try not to disturb your beautifully arranged fruit on the bottom of the pan while doing this.
  2. Bake: It will take about 40-45 minutes to bake the pineapple upside down cake. It should look nice a golden brown on top and a toothpick inserted into the center of the cake should come out clean when the cake is done. Don’t flip it out right away! Waiting 5-10 minutes gives the cake just a little time to set up a bit so it doesn’t fall apart when you turn it out.
  1. Flip the cake upside down: This is the fun part! Grab a serving plate or cake stand and place it upside down on top of your cake pan. Then run a knife around the edge of the pan and CAREFULLY (the pan is still hot so you need to use oven mitts) flip both the plate and pan over. You might need to wait 20-30 seconds, but the cake should just drop right out of the pan. If any of the fruit sticks to the pan, use a fork or knife to loosen it and place it back in its spot on top of the cake. Ta-DA!

I recommend serving pineapple upside down cake either warm or room temperature. Some people like it cold out of the fridge, but I think the flavors are much better when they aren’t chilled.

It doesn’t need any decoration at all, but if you want to be extra fancy you can pipe a swirl of freshly whipped cream on top. Or serve it with a small scoop of vanilla, toasted almond, or maple walnut ice cream on the side.

Can this recipe be made in a 9×13-inch pan?

If you have a larger group or are taking this cake to a potluck, I recommend doubling all of the ingredients and baking the cake in a 9×13-inch cake pan. The bake time should be about the same at around 40-45 minutes. Just be sure to have a large rectangular pan to turn the cake out onto! A clean baking sheet might not be the prettiest for presentation, but it works just great!

Storage and Freezing Instructions

  • Storage: Cover any uneaten cake in an airtight container and it will keep well on the counter or in the fridge for 2-3 days. I like to warm up individual slices in the microwave for a few seconds before enjoying so it tastes like it is fresh out of the oven. Or cover multiple pieces with foil and warm in a 350 degree F oven for 5-10 minutes if you are reheating multiple slices of cake.
  • Freezing: This cake will freeze well for up to 2 months if properly stored. First let it cool completely, then wrap in two layers of plastic wrap and place in a freezer safe bag before freezing. Thaw the frozen cake on the counter for at least 2-3 hours before rewarming in a 350 degree F oven for 5-10 minutes before serving.

Frequently Asked Questions

Can I use fresh pineapple?

Technically yes, however it’s not something I recommend as it will release more liquid, which can affect the cake. If you really want to use fresh pineapple, I recommend cutting it up and roasting it for 10 minutes on a baking sheet first, then patting well with paper towels before using in this recipe.

Can I use pineapple tidbits?

Yes, if you only have pineapple chunks or tidbits on hand, you can use those instead of the pineapple rings. All-in-all it is about 1 1/2 cups of fruit.

How do you keep pineapple upside down cake from getting soggy?

The best way to keep your cake from getting soggy is to not only drain the pineapple and cherries well, but to pat them dry on paper towels before using them.

When should I flip my pineapple upside down cake?

You want to let the cake sit for 10 minutes before flipping it out. This gives it enough time to set up a bit so you aren’t turning out a super hot cake and risking it falling apart, but it’s also soon enough that the caramelized brown sugar and fruit on the bottom will come out and not stick to the pan. If you wait much longer than 10-15 minutes, the brown sugar cools too much and you will likely loose much of the delicious topping.

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a from scratch pineapple upside down cake with pineapple and cherries
Yield: 8 servings

Pineapple Upside Down Cake

Pineapple Upside Down Cake is an old-fashioned recipe that is absolutely delicious with a buttery, moist crumb and sweetly caramelized fruit on top that makes for a beautiful presentation without a need for additional decoration! Serve it warm or room temperature with whipped cream or a small scoop of vanilla ice cream for a special treat!

Prep Time 15 minutes
Cook Time 30 minutes
Total Time 45 minutes

Ingredients

Topping

  • 1/2 cup brown sugar
  • 1/4 cup melted butter
  • 1 (20-ounce) can sliced pineapple rings, drained, reserving juice
  • 20 maraschino cherries, without stems

Cake

  • 1/2 cup salted butter, softened
  • 1/2 cup granulated sugar
  • 1/4 cup brown sugar packed
  • 1 large egg
  • 1/4 cup sour cream, room temperature
  • 1/4 cup milk
  • 1/4 cup pineapple juice
  • 1 teaspoon vanilla extract
  • 1 and 1/2 cups cake flour
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon salt

Instructions

  1. Preheat oven to 350 degrees F. Spray a 9-inch cake pan with baking spray. Drain the pineapple (reserving 1/4 cup of the juice) and pat the pineapple rings and maraschino cherries dry on paper towels.
  2. Combine the brown sugar and melted butter in a small bowl, then spread into the bottom of the prepared pan. Arrange seven of the pineapple slices in the bottom of the pan, then cut the others in half and place them along the sides of the pan, filling in holes with the maraschino cherries.
  3. In a large bowl, beat the butter, granulated sugar, and brown sugar until creamy and light. Add the egg, sour cream, milk, pineapple juice, and vanilla and mix again, scraping down the sides of the bowl. The batter may start looking curdled, but that's okay.
  4. Add the flour, baking powder, and salt, then mix until combined. The batter will be fairly thick. Spoon the batter over the fruit and spread it into an even layer.
  5. Bake for 40-45 minutes, just until a toothpick inserted into the center of the cake comes out clean and the cake is golden brown on top. Let cool for 5-10 minutes before turning out onto a serving plate. Loosen the sides of the cake from the pan first by running a thin, sharp knife around the edges. Then place your serving plate upside down on top of the cake pan before flipping both over. The cake will drop right out of the pan, although you may have a piece of fruit or two that likes to stick. If so, just lift it out and place it back on top of the cake.
  6. Serve warm or at room temperature.

Notes

  • Store any uneaten cake in an airtight container on the counter or in the fridge for 2-3 days. To reheat, you can warm individual slices in the microwave for a few seconds or cover with foil and warm in a 350 degree F oven for 5-10 minutes.
  • Freezing: You can freeze this cake for up to 2 months. Let it cool completely, then wrap in plastic wrap before freezing. Thaw on the counter before rewarming in a 350 degree F oven for 5-10 minutes before serving.
  • I don't recommend using fresh pineapple for this cake as it releases more liquid than canned pineapple, which can make for a soggy cake. If you only have pineapple chunks or tidbits on hand, you can use those instead of rings. You need about 1 1/2 cups of fruit.

Nutrition Information:

Yield:

8

Serving Size:

1

Amount Per Serving: Calories: 372Total Fat: 20gSaturated Fat: 12gTrans Fat: 1gUnsaturated Fat: 6gCholesterol: 74mgSodium: 400mgCarbohydrates: 49gFiber: 1gSugar: 40gProtein: 2g

All nutritional information is based on third party calculations and is only an estimate. Each recipe and nutritional value will vary depending on the brands you use, measuring methods and portion sizes per household.

Monday #SpringSweetsWeek Recipes

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