Pineapple Upside-Down Cake

This pineapple upside-down cake is a Southern classic. Topped with pineapple slices, maraschino cherries, and crunchy pecans, it’s just like how Grandma used to make it.

A pineapple upside-down cake on a white plate with a slice taken out

Adapted from White Lily Flour | The White Lily Cookbook | White Lily, 2021

Southerners can’t look twice at a can of pineapple rings without thinking of a fresh pineapple upside-down cake. Break out your cast-iron skillet for this delicious treat.—White Lily Flour

Pineapple Upside-Down Cake FAQs

I don’t have a cast-iron skillet. Can I make this in a regular cake pan?

Yes, but increase cooking time by 5 to 10 minutes.

How long should I wait before flipping the cake?

Wait five minutes before flipping this upside-down cake out of its pan. Waiting much longer can allow the caramelized sugar in the pineapple slices to stick and cause the cake to stick. As you can see from our testers’ reviews, just about all of them had no problem with the cake sliding out of the pan.

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

The reason why some pineapple upside-down cakes are soggy is moisture on the pineapple slices and maraschino cherries. Fully drain the can of pineapple slices (save the juice, it’s delicious!) and blot them dry.

Isn’t the red dye in maraschino cherry harmful to your health?

Absolutely not. The manufacturers of maraschino cherries use FD&C Red Dye #40. That’s the same dye used in Doritos, your favorite chewing gum, food coloring, and Easter-egg dye. Red Dye #3 is the culprit related to health concerns. If you’re still leery, you can do what recipe tester Adrienne Lee did (photo below) and use Amarena Fabri wild cherries in syrup.

A pineapple upside-down cake on a white plate

Pineapple Upside-Down Cake

A pineapple upside-down cake on a white plate with a slice taken out
Southerners can’t look twice at a can of pineapple rings without thinking of a fresh pineapple upside-down cake. Break out your cast-iron skillet for this delicious treat.
White Lily Flour

Prep 30 mins
Cook 40 mins
Total 1 hr 15 mins
Dessert
American
8 servings
652 kcal
5 from 1 vote
Print RecipeBuy the The White Lily Cookbook cookbook

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Ingredients 

  • 2 sticks (8 oz) unsalted butter at room temperature, plus 4 tablespoons (2 oz), divided
  • 3/4 cup firmly packed light brown sugar
  • 5 to 7 canned pineapple rings
  • 7 maraschino cherries
  • 1/2 cup chopped pecans
  • 1 cup granulated sugar
  • 2 large eggs at room temperature
  • 1 teaspoon vanilla extract
  • 2 cups all-purpose flour
  • 2 teaspoons baking powder
  • 1/2 teaspoon table salt
  • 3/4 cup whole milk at room temperature

Directions
 

  • Preheat oven to 350°F (180°C).
  • In a 10-inch (25-cm) cast-iron skillet, place 4 tablespoons butter. Place in oven until butter is melted.
  • Sprinkle brown sugar over butter in skillet. Arrange pineapple rings on top. Place 1 cherry in the center of each pineapple ring. Scatter pecans around pineapple rings in any open spaces.
  • In the bowl of a fitted with the paddle attachment, beat remaining 2 sticks of butter and granulated sugar at medium speed until fluffy, 3 to 4 minutes, stopping to scrape sides of bowl. Add eggs, one at a time, beating well after each addition. Beat in vanilla.
  • In a medium bowl, whisk together flour, baking powder, and salt. With mixer on low speed, gradually add flour mixture to butter mixture alternately with milk, beginning and ending with flour mixture, beating just until combined after each addition.
  • Pour batter over pineapple rings, smoothing top with an offset spatula.
  • Bake until a wooden toothpick inserted in the center comes out clean, 30 to 40 minutes. Let cool in pan for 5 minutes.
  • Run a knife around the edge of the pan to release sides of cake and carefully invert cake onto a flat serving plate. Serve warm or at room temperature.
Print RecipeBuy the The White Lily Cookbook cookbook

Want it? Click it.

Show Nutrition

Serving: 1sliceCalories: 652kcal (33%)Carbohydrates: 79g (26%)Protein: 7g (14%)Fat: 36g (55%)Saturated Fat: 19g (119%)Polyunsaturated Fat: 3gMonounsaturated Fat: 11gTrans Fat: 1gCholesterol: 125mg (42%)Sodium: 185mg (8%)Potassium: 292mg (8%)Fiber: 2g (8%)Sugar: 53g (59%)Vitamin A: 1011IU (20%)Vitamin C: 3mg (4%)Calcium: 120mg (12%)Iron: 2mg (11%)
Lodge 10-1/4-Inch Pre-Seasoned Skillet

Lodge 10-inch Pre-Seasoned Cast Iron Skillet, from Amazon

Recipe Testers’ Reviews

In some ways, this is a very traditional pineapple upside-down cake. The cake has a light vanilla flavor and is also dense like a coffee cake. Plus, the look of the finished cake is traditional. The flavors are traditional. What’s great is that it also tastes good. 

The only difficult part was putting the chopped pecans between the rather large pineapple rings. On the other hand, the caramelized pecans were not as attractive but quite tasty. After the 5 minutes of cooling, the cake came out easily from the pan and only a few pecans were left on the pan (easily scraped off and added). This recipe is definitely worth making. 

As a side note, I don’t have traditional maraschino cherries. Instead, I have the expensive Italian cherries in syrup from Italy. I substituted those cherries and they worked equally well and added to the flavor.

I’ve never made a pineapple upside-down cake or any cake in a cast-iron skillet, for that matter. 

However, after all my ingredients were out, the eggs were at room temperature, and the butter softened I realized I no longer own a cast-iron skillet. (I loaned it to a friend and it wasn’t returned.)  I continued the recipe using a 10-inch cake pan. The cake wasn’t done after 35 minutes, so I increased the cooking time by 7 minutes (I assume using a cake pan instead of the skillet contributed to the increased cooking time.)

In the end, the cake looked good and tasted great. I’d make this again.

I liked that the cake had chopped pecans in the spaces between the pineapple slices. And I think I will make this a regular addition to my pineapple upside-down cakes in future. I would have liked to have been able to put more pineapple slices on the bottom of my cake-I only managed 4 1/2 slices. Also, I found that when I turned my cake out part of the top stayed in the non-stick skillet. If I were making the cake again, I might cut a circle of parchment paper to put on the bottom of the pan to try to help the cake out in one piece. I would definitely make the cake again and would recommend the recipe to others.

The ubiquitous pineapple upside-down cake. You ask, is there really room for one more recipe? Well, one mouthful of this scrumptious pineapple upside-down cake, and you’ll be instantly transported to a true Southern covered-dish Sunday supper! 

For me, this recipe checked all the boxes and more. First, the 10-inch cast-iron skillet was a perfect size for the amount of batter and produced a welcomed slightly crunchy texture to the cake’s exterior. After baking then cooling the cake for 5 mins, it effortlessly slipped out of the skillet, totally intact when flipped. Each mouthful was nothing but pure Southern gooey goodness. Caramelized fresh pineapple rings and maraschino cherries adorned the warm, buttery, moist crumb. The addition of the pecans, which I toasted, offered a warm, nutty flavor and seemed to minimize any excessive sweetness. I may even add more next time.  Finally, this is my favorite go-to recipe for pineapple upside-down cake. Now, if I can only figure out where and what time supper is!

A picture-perfect cake, a recipe that goes back years. And it’s a holiday tradition for many generations on grandma’s cake plate. The cake is very tender and buttery. What I liked about this recipe is it is quick to put together, you can serve it within 15 minutes of coming out of the oven, and brown sugar and butter baking make your home smell so sweet.

You’ll appreciate how easy and cleanly it comes out of the pan. The topping is not exceedingly sweet nor overpowers the pineapple. Also, I used Kerry Gold butter and would suggest a high-quality butter, as you can really taste it.

Originally published February 14, 2022

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Comments

  1. It might be easier and quicker to simply cover the whole top of the cake with a slightly larger quantity of chopped pecans and then top the pecans with the pineapple and cherries, pressing them into the batter slightly. On the other hand, the pecans might cause the pineapple rings to separate from the top of the cake when unmolding it. Seemed like a good idea at the time.

    1. I can see how it would be definitely easier, Rita. But then there wouldn’t be any of that lovely pineapple caramelization.

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