Old Fashioned Pineapple Upside Down Skillet Cake

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There’s something so nostalgic about an old-fashioned pineapple skillet cake. This timeless dessert, with its caramelized pineapple rings and cherries topping a moist light cake, brings back childhood memories of family gatherings. It’s so delicious and visually impressive!

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• Prep time: 20 minutes
• Baking time: 40 to 50 minutes
• Cool time: 30 minutes
• Total time: 1 hour + 40 minutes
• Servings: 8 to 10
• Preparation level: Beginner +

This pineapple cake is made in a cast-iron skillet with simple ingredients and is perfect for any occasion! It was a favorite cake of mine growing up and I still love it such as much today!

Ingredient Notes

• Butter: Unsalted butter forms the bast of your caramel topping. Don’t skimp on it, this is what gives the pineapple that golden, glossy coating.
• Brown sugar: Combined with butter to create the rich, sticky base. Dark brown sugar will give you a deeper flavor, while light brown sugar is a bit lighter in taste.
• Fresh pineapple: Fresh pineapple adds a juicer texture and brighter flavor than canned, but canned slices can be used.
• Maraschino cherries: Optional but traditional. Press them into the center of each pineapple ring for that classic vintage look and taste.
• Eggs: Let them come to room temperature so they incorporate smoothly.
• Flour: Stick with all-purpose flour. Measure properly to keep the cake light and tender.

Step-by-Step Instructions

• If using fresh pineapple, prep the pineapple by using a pineapple corer and slicer tool or a large kitchen knife.
• Save the juice by squeezing the outer shell together and catching the juice in a small bowl. Set aside.

• Warm a cast iron skillet over medium heat. Add the butter and completely melt.
• Add the brown sugar to the melted butter. As the brown sugar begins to melt, spread evenly over the bottom of the skillet. Turn off the stove flame.

• Arrange the pineapple slices close together in a single layer over the brown sugar mixture. Add a maraschino cherry in the center of each pineapple slice.

• Separate the eggs and place the egg yolks in a large bowl.
• Beat egg yolks at medium speed until they begin to thicken. Gradually add the white sugar, beating until combined.

• Add the vanilla extract and gradually add the reserved pineapple juice to the egg yolk mixture, beating until blended.
• In a small bowl combine flour and baking powder. 
• Reduce the electric mixer speed and gradually add the flour mixture to the wet ingredients. Beat on low speed until fully mixed.

• In another small bowl, beat egg whites until stiff peaks are formed. 
• Fold egg whites into the batter until fully incorporated.

• Carefully spoon the cake batter evenly over the pineapple slices.
• Bake in a preheated oven. The cake is done when a cake tester is placed in the center of the cake and it comes out clean.

• Remove from oven and place skillet on a wire rack to cool.

• Invert the cake onto a large serving plate.

See recipe card below for complete measurements and baking times.

Serving suggestions

Add a dollop of whipped cream or a scoop of vanilla ice cream. Serve warm or chilled.

Laura Belle’s Tips

1. A well seasoned 9-inch cast iron skillet can be used – The outcome will be a little thicker cake. Just be sure it is large enough that the cake doesn’t overflow. 
2. Using a coring tool will give you pineapple rings – You can use a large knife to prep the pineapple and cut 2 to 3-inch pieces for the top of the cake.
3. Don’t overmix the batter – mix until just combined for a tender fluffy cake. Overmixing can lea to a dense texture.
4. For a little extra flavor – add additional cherries in every open space there is around the slices of pineapple.
5. Use a serving platter – wider than the skillet when inverting the cake.

Make Ahead

This cake can be made 1 to 3 days ahead. After the cake has cooled to room temperature, securely cover the platter with plastic wrap or use a large pie carrier and store it in the refrigerator. 

Storing

If you have any leftovers in an airtight container for up to 5 days in the fridge.

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Yield: 8 to 10 Servings

Old Fashioned Pineapple Upside Down Skillet Cake

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A timeless dessert with caramelized pineapple rings and cherries topping a moist cake. Made in a cast-iron skillet and perfectly delicious!

Prep Time 20 minutes

Cook Time 45 minutes

Additional Time 30 minutes

Total Time 1 hour 35 minutes

Ingredients

• 1/4 cup butter – unsalted
• 2/3 cup brown sugar (light or dark) – firmly packed
• 7 to 9 pineapple sliced rings (fresh pineapple or 1 – 20 ounce can)
• Maraschino cherries (remove stems and use at least 7 or more)
• 2 large eggs (at room temperature and separated)
• 3/4 cup granulated sugar
• 1/4 cup pineapple juice (saved from the fresh fruit or canned)
• 1 teaspoon vanilla extract
• 3/4 cup all-purpose flour
• 1/2 teaspoon baking powder

Instructions

1. Heat oven to 325 degrees F.
2. If using fresh pineapple, prep the pineapple by using a pineapple corer and slicer tool or a large kitchen knife. (see Helpful Tips)
3. Save the juice by squeezing the outer shell together and catching the juice in a small bowl. Set aside.
4. Warm a cast iron skillet over medium heat. Add the butter and completely melt.
5. Add the brown sugar to the melted butter. As the brown sugar begins to melt, spread evenly over the bottom of the skillet.
6. Turn off the stove flame.
7. Arrange the pineapple slices close together in a single layer over the brown sugar mixture. Add a maraschino cherry in the center of each pineapple slice. (see Helpful Tips)
8. Separate the eggs and place the egg yolks in a large bowl. Beat egg yolks at medium speed until they begin to thicken. Approximately 1 minute. Gradually add the white sugar, beating until combined.
9. Add the vanilla extract and gradually add the reserved pineapple juice to the egg yolk mixture, beating until blended.
10. In a small bowl combine flour and baking powder. 
11. Reduce the electric mixer speed and gradually add the dry ingredients to the wet ingredients. Beat on low speed until fully mixed.
12. In a separate bowl, beat egg whites until stiff peaks are formed. Approximately 4 minutes.
13. Fold egg whites into the batter until fully incorporated.
14. Carefully pour batter evenly over the pineapple slices.
15. Bake for 40 to 50 minutes. Check the doneness of the cake with a cake. It should come out clean.
16. Cool cake on a wire rack in the skillet for 30 minutes.
17. Invert the cake onto a large serving plate. (see Helpful Tips)
18. Serve warm.

Notes

Helpful Tips

• A 9-inch cast iron skillet can be used. The outcome will be a thicker cake. Just be sure it is large enough that the cake doesn't overflow. 

• Using a coring tool will give you pineapple rings. If you use a large knife to prep the pineapple, you can cut 2 to 3-inch pieces for the top of the cake.

• If you want a little extra flavor, add additional cherries in every open space there is around the slices of pineapple.

• Use a serving platter that is wider than the skillet when inverting the cake.

Serving suggestions

​Add a dollop of whipped cream or a scoop of vanilla ice cream.

Serve warm or chilled.

This cake can be made 1 to 3 days ahead. After the cake has cooled to room temperature, securely cover the platter with plastic wrap or use a large pie carrier and store it in the refrigerator. 

Nutrition Information:

Yield:

10

Serving Size:

1
Amount Per Serving: Calories: 273Total Fat: 6gSaturated Fat: 3gTrans Fat: 0gUnsaturated Fat: 2gCholesterol: 49mgSodium: 81mgCarbohydrates: 55gFiber: 2gSugar: 42gProtein: 3g

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