A true classic, this vintage Pineapple Upside Down Cake has been a favorite for generations. Soft, buttery cake topped with caramelized pineapple rings and maraschino cherries—this from-scratch recipe will bring back warm memories and is easily the best pineapple upside-down cake you’ll make. This recipe yields one round cake.
I remember my mother making an easy pineapple upside-down cake from a boxed mix in a 9×13 pan. I always loved how sunny and cheerful it looked—perfect for gatherings and simple family dinners.
A few years ago I was reminded of this cake while reading the Janet Evanovich Stephanie Plum novels. Stephanie’s big sweet tooth and the way her family lures her home with pineapple upside-down cake inspired me to finally share my own from-scratch version on the site. I first published this recipe in 2015 and it remains a favorite.
Why You’ll Love This Pineapple Upside Down Cake
This classic cake combines a tender, buttery crumb with sweet, sticky caramelized pineapple and bright cherries on top. Baked from scratch with simple pantry ingredients, it looks elegant while staying delightfully nostalgic. The shiny pineapple rings and cherries give it a picture-perfect finish.
A Bit of History
The pineapple upside-down cake became popular in the 1920s after canned pineapple rings became widely available in the United States. A recipe contest held to promote canned pineapple helped popularize the idea of baking pineapple in a cake and flipping it over for serving.
Ingredients
This cake uses common pantry staples to create a moist, flavorful dessert. For the full, printable recipe, see the recipe card below.
- All-purpose flour – a pantry essential
- Baking powder – helps the cake rise
- Fine salt – enhances flavor
- Unsalted butter – divided; use salted and reduce added salt if needed
- Granulated sugar
- White vinegar – or apple cider vinegar as a substitute
- Vanilla – real extract preferred
- Eggs
- Low-fat buttermilk – or make your own by adding 1 Tbsp vinegar to 1 cup milk
- Brown sugar – light brown works well
- Brandy – or substitute apple juice
- Canned pineapple rings – drain well and save the juice if you like
- Maraschino cherries – for classic presentation; dried or frozen cherries can be used in a pinch
How to Make Pineapple Upside Down Cake
Prep
Preheat the oven to 350°F. Sift together the flour, baking powder, and salt in a medium bowl and set aside.
Mix
In a mixer fitted with a paddle attachment, cream 12 tablespoons of butter with the granulated sugar, 1 tablespoon vinegar, and 2 teaspoons vanilla until light and fluffy (about 3–4 minutes). Add the eggs one at a time, beating after each addition. On low speed, add the dry ingredients alternately with the buttermilk in three additions, scraping the bowl as needed. Increase speed to medium and beat until the batter is smooth, about 3 minutes. Set aside.
Prepare the Topping
In a 10″ skillet or small saucepan over medium heat, melt the remaining butter. Whisk in the remaining vanilla, the brown sugar, and the brandy until dissolved. Remove from heat. Arrange pineapple slices in a single layer over the bottom of the skillet and place cherries evenly among the rings.
Bake
Gently pour the batter over the pineapple and cherries, smoothing the top as needed. Bake until the cake is golden and a toothpick inserted in the center comes out clean, about 45–50 minutes (ovens vary).
Allow the cake to cool for 30 minutes, then invert onto a serving plate. The caramelized pineapple and cherries should glisten—serve warm or at room temperature.
Tips & Tricks
- Have ingredients measured and ready before you start.
- Drain pineapple and cherries thoroughly to avoid a soggy topping; pat dry if needed.
- Bring eggs and butter to room temperature for a smoother batter.
Storage
Stored at room temperature in an airtight container, this cake will keep well for about two days. Refrigerated in an airtight container, it will last up to five days.
Frequently Asked Questions
What pan works best? A round cake pan or a cast-iron skillet both work well for this recipe.
Why might my cake be soggy? Excess moisture from the pineapple or cherries can cause sogginess. Make sure to drain and pat them well.
Why is it called an upside-down cake? Because the fruit and caramel are placed on the bottom of the pan before baking, and the cake is inverted for serving so the fruit becomes the top.
Can I make it gluten-free? Yes—substitute a reliable 1:1 gluten-free flour blend such as Cup4Cup or Bob’s Red Mill.
Can I use fresh pineapple? Absolutely. If using fresh slices, drain or pat them dry to remove excess moisture before arranging.
This from-scratch Pineapple Upside Down Cake is buttery, sweet, and comfortingly nostalgic. Ready to bake? Scroll to the recipe card below for exact measurements and step-by-step instructions.
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{from scratch} Pineapple Upside Down Cake
10 mins
50 mins
1 hr
2 hrs
Ingredients
- 1 3/4 cups flour
- 2 teaspoon baking powder
- 1/4 teaspoon fine salt
- 1 1/3 cups unsalted butter, divided
- 1 cup granulated sugar
- 1 Tablespoon white vinegar
- 3 teaspoon vanilla, divided
- 3 eggs
- 1 1/3 cup low-fat buttermilk
- 10 Tablespoons brown sugar (5/8 cup)
- 2 Tablespoons brandy (or apple juice)
- 7 slices canned pineapple
- 1 1/2 cup stemmed maraschino cherries
Instructions
- Preheat the oven to 350° F.
- Sift together the flour, baking powder, and salt. In a mixer bowl, cream together 12 Tablespoons butter, granulated sugar, vinegar, and 2 teaspoons vanilla until fluffy (3–4 minutes). Add eggs one at a time, beating after each. On low speed, alternately add the flour mixture and buttermilk in three batches, scraping the bowl as needed. Beat on medium until smooth (about 3 minutes).
- In a 10″ nonstick skillet over medium heat, melt remaining butter. Whisk in the remaining vanilla, brown sugar, and brandy until dissolved. Remove from heat and arrange pineapple slices in a single layer; place cherries evenly among the rings.
- Gently pour the batter over the pineapple and cherries. Bake until golden and set, about 45–50 minutes. Test with a toothpick in the center; it should come out clean.
- Let cool for 30 minutes, then invert onto a serving plate and enjoy.
Nutrition
This recipe was originally posted on July 12, 2015 and updated to improve user experience and presentation on June 28, 2022.
The recipe originated with A Spoonful of Thyme and was adapted for sharing then and again here for readers who love classic, homemade desserts.
