Pineapple Upside-Down Cake Recipe

In 1925, the Hawaiian Pineapple Company ran a recipe contest that drew more than 60,000 entries, and 2,500 of them were variations on the same cake: a butter cake baked upside down over caramel and canned pineapple rings. The winning entry came from Mrs. Robert Davis of Norfolk, Virginia, and the corporate campaign that followed cemented pineapple upside-down cake as a national classic. The recipe below is the version that has survived a century of home kitchens, written for a 10-inch cast iron skillet with the technique most home cooks miss: invert while still hot.

What You’ll Need

A 10-inch cast iron skillet (or a 9-inch round cake pan with 2-inch sides), a stand mixer for the creamed butter and sugar, an offset spatula to spread the batter without disturbing the pineapple pattern, and a fine mesh strainer for draining the canned rings thoroughly so the caramel does not go soupy.

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Where Pineapple Upside-Down Cake Came From

In 1903, James Dole’s Hawaiian Pineapple Company produced the first commercially profitable canned pineapple, and for nearly a decade the fruit reached the mainland in awkward, hand-cut chunks. The change came between 1911 and 1913, when engineer Henry Gabriel Ginaca built and patented a machine that cored, peeled, and sliced pineapples into uniform rings at more than 50 per minute. The Ginaca machine took home a gold medal at the 1915 Panama-Pacific Exposition, and the cleanly round canned ring became the shape of pineapple in American kitchens. The cake we now think of as pineapple upside-down cake is, structurally, built around that ring.

The cake itself was made famous in 1925, when the Hawaiian Pineapple Company (later Dole) ran a national recipe contest that drew more than 60,000 entries. Of those, roughly 2,500 were variations on the same butter-cake-over-caramel format, and the winning entry came from Mrs. Robert Davis of Norfolk, Virginia. Dole launched a national advertising campaign on the back of the contest, and by the mid-1930s pineapple upside-down cake had moved into the rotation of nearly every American home baker. By the 1950s, the maraschino cherry in the center of each ring had been added to the canonical look, and the dish settled into its final identity: a homey, deeply American dessert with a Hawaiian origin story.

A Few Notes on the Ingredients

• Unsalted butter and brown sugar: The caramel base is two ingredients only. No corn syrup, no molasses. As the cake bakes, the sugar dissolves into the butter and the pineapple juice that weeps from the rings, creating a shiny golden caramel that sets just firmly enough to hold the fruit when inverted.
• Canned pineapple rings: Fresh pineapple weeps too much water into the caramel and turns the topping soupy, and it contains bromelain, an enzyme that can interfere with the cake structure. Canned rings come pre-sliced to the iconic Ginaca shape, drained of most of their moisture, and hold their pattern through the bake and the flip.
• Maraschino cherries: Not an afterthought. The kitschy 1950s visual is the wedge. Drop a cherry into the hole of every ring before the batter goes over the top and own the look.
• Buttermilk: Buttermilk gives the crumb a faint tang that cuts the sweetness of the caramel and produces a more tender bite than oil-based recipes.
• Reserved pineapple juice: A quarter cup of the drained juice goes into the batter alongside the buttermilk, reinforcing the pineapple flavor through the cake itself.
• 10-inch cast iron skillet: Bake in cast iron for browned, slightly crisp edges, or use a 9-inch round cake pan with 2-inch sides for a cleaner, taller presentation. Either works.
• Inversion window: Cool the cake exactly 10 minutes, run a knife around the edge, then flip. Wait any longer and the caramel sets like glass and the cake locks in.

Recipe: Pineapple Upside-Down Cake

Prep time: 25 minutes | Cook time: 38 minutes | Total time: 1 hour 5 minutes (plus 10 minute cool) | Serves: 8

Ingredients

For the caramel base:

• 6 tbsp (85 g) unsalted butter
• 1 cup (200 g) packed light brown sugar
• 1 can (20 oz / 565 g) pineapple rings, drained (reserve 1/4 cup juice)
• 10 to 12 maraschino cherries

For the cake:

• 1 1/2 cups (190 g) all-purpose flour
• 1 1/2 tsp baking powder
• 1/2 tsp salt
• 1/2 cup (113 g) unsalted butter, softened
• 3/4 cup (150 g) granulated sugar
• 2 large eggs
• 1 tsp vanilla extract
• 1/2 cup (120 ml) buttermilk
• 1/4 cup (60 ml) reserved pineapple juice

Instructions

1. Heat the oven to 350°F (175°C) and set a rack in the middle.
2. For the caramel: melt the 6 tablespoons of butter directly in a 10-inch cast iron skillet over medium heat. Sprinkle the brown sugar evenly over the butter and stir gently until it dissolves into a shiny, bubbling layer, about 1 to 2 minutes. Remove from the heat.
3. Arrange the drained pineapple rings on top of the caramel in a single, snug layer (one ring in the center, the rest around it). Drop a maraschino cherry into the hole of each ring. Set the skillet aside.
4. For the cake: whisk the flour, baking powder, and salt together in a medium bowl and set aside.
5. In the bowl of a stand mixer fitted with the paddle, cream the softened butter and granulated sugar on medium-high speed for 4 minutes, scraping the bowl once, until pale and light.
6. Add the eggs one at a time, beating well after each, then beat in the vanilla.
7. In a small measuring cup, combine the buttermilk and reserved pineapple juice. With the mixer on low, add the dry ingredients in three additions, alternating with the buttermilk-juice mixture in two additions, starting and ending with the dry. Mix only until the batter is smooth; do not overmix.
8. Pour the batter evenly over the pineapple in the skillet and smooth the top with an offset spatula, working gently so you do not disturb the ring pattern underneath.
9. Bake on the middle rack for 35 to 40 minutes, until the top is golden and a skewer inserted into the center comes out clean (or with a few moist crumbs).
10. Cool the skillet on a rack for exactly 10 minutes. No longer. Run a thin knife around the edge of the cake to release it from the skillet.
11. Place a serving platter, upside down, over the skillet. In one confident motion, flip the skillet and platter together. Lift the skillet straight up. If a piece of pineapple or some caramel sticks to the skillet, scrape it off with a spoon and patch it onto the cake while warm. If the caramel has set too firm to release, return the whole skillet to a 350°F (175°C) oven for 2 to 3 minutes to re-melt it, then flip immediately.
12. Serve warm with vanilla ice cream or lightly whipped cream.

Notes

The 10-minute cool is the most important step in the entire recipe. Cooler than that and the caramel begins to set into glass, locking the cake into the skillet and tearing the fruit when you finally flip. Set a timer the moment the skillet comes out of the oven, and trust it. If you accidentally let it cool longer, the oven-rewarm trick (2 to 3 minutes back in the 350°F oven) brings the caramel back to a releasable temperature without overbaking the cake.

To scale this for a crowd in a 9×13 pan, double the cake batter and the caramel base, use two 20 oz cans of pineapple rings (about 18 to 20 rings total), and bake at 350°F (175°C) for 40 to 45 minutes. The 10-minute cool window still applies, and the flip is harder with a rectangular pan; line the bottom with parchment with a 2-inch overhang on the long sides so you can lift the cake out instead of trying to invert the whole pan in a single motion.

Leftovers keep covered at room temperature for up to 2 days, or refrigerated up to 5. Refrigerate only if you must; the caramel firms in the cold and the cake reads slightly drier. Bring slices back to room temperature, or warm them gently in a 300°F (150°C) oven for 5 to 7 minutes before serving.

Tips and Variations

Why Canned Pineapple Beats Fresh for This Format

Food magazines love to default to fresh as the upgrade. For this cake it is the wrong move. Fresh pineapple holds 80-plus percent water by weight, and most of that water finds its way into the caramel during the bake, turning the brown sugar layer thin and soupy instead of shiny and set. Fresh pineapple also contains bromelain, an enzyme that can soften the cake’s gluten structure and leave you with a slightly gummy crumb at the fruit interface. Canned rings are drained, pre-cooked, and shaped to the exact pattern that defines the visual identity of the dish; they are not a compromise, they are the correct ingredient. The Ginaca-machine ring is the cake.

The 10-Minute Inversion Window That Most Recipes Skip

Most home cooks who have a bad experience with this cake have the same complaint: half the pineapple stayed in the pan. The cause is almost always the same. They waited 20 or 30 minutes before flipping, or they let the cake cool completely, and by the time they tried to invert, the brown sugar caramel had cooled past 200°F (93°C) and had recrystallized into a hard, sticky glass that bonded the fruit to the bottom of the pan. The fix is structural, not skill-based: flip at exactly 10 minutes. Set a timer. If you blow past it, the oven-rewarm rescue (2 to 3 minutes at 350°F) re-melts the caramel and gives you a second chance.

Cast Iron vs Round Cake Pan Decision

A 10-inch cast iron skillet is the traditional move and the one this recipe is written for. The skillet conducts heat aggressively, browns the edges, and lets you melt the butter and build the caramel directly over the burner without dirtying a second pan. A 9-inch round cake pan with at least 2-inch sides works almost as well; you melt the butter separately and pour it into the pan first. The skillet version produces a slightly browner, more rustic edge; the round pan gives you a taller, cleaner-looking slice. Pick by what you already own. Avoid anything shallower than 2 inches, and avoid springform pans entirely , the caramel will leak.

Adding Toasted Pecans to the Caramel Base

For a butter-pecan upside-down cake, scatter 60 g (about 1/2 cup) of toasted, roughly chopped pecans across the caramel before you arrange the pineapple rings. Toast the pecans first in a dry skillet for 4 to 5 minutes until they smell nutty; raw pecans go soft and steamy in the caramel and lose their texture. The pecans tuck into the spaces between the rings and the centers of the cherries, and they end up on top of the inverted cake as a second layer of texture. Walnuts work too, though they are slightly more bitter. Macadamias are excellent if you want to lean further into the Hawaiian provenance of the dish.

Make-Ahead and Storage Strategy

The cake is best the day it is baked, while the caramel is still slightly warm and shiny. If you need to make it ahead, bake it the morning of, cool to room temperature, and cover loosely with foil; reheat the whole cake in a 300°F (150°C) oven for 8 to 10 minutes before serving. Do not refrigerate if you can avoid it. For longer storage, slice the cooled cake, wrap each slice individually in plastic, and freeze for up to 3 months. Thaw slices on the counter for 1 to 2 hours, then warm gently in the oven. The freezer does the caramel surprisingly few favors, but the cake survives.

What to Serve It With

Pineapple upside-down cake belongs on the Easter dessert table , the yellow-and-cherry palette is built for spring, and it is lighter and more festive than carrot cake or pound cake without losing the celebratory feel. It is also the right cake for a retro dinner party or any 1950s-themed evening, where the kitschy visual is the entire point. Day to day, it makes a strong tea-time slice with black tea or a flat white. For dessert proper, serve it warm with a scoop of good vanilla ice cream, lightly sweetened whipped cream, or a spoonful of crème fraîche to cut the sweetness of the caramel.

Frequently Asked Questions

Canned or fresh pineapple , which works better?

Canned, every time. Fresh pineapple weeps too much water into the caramel and turns the topping soupy; it also contains bromelain, an enzyme that can soften the cake structure. Canned rings come pre-shaped to the iconic Ginaca-machine ring, are drained of most of their moisture, and hold their pattern through the bake and the flip. For this specific format, canned is the correct ingredient.

Why did this cake become an American classic?

The 1925 Dole recipe contest. The Hawaiian Pineapple Company drew more than 60,000 entries, and 2,500 of them were variations on the upside-down cake format. The winning entry from Mrs. Robert Davis of Norfolk, Virginia, plus the corporate ad campaign that followed, put the dish on the radar of nearly every American home baker by the 1930s. By the 1950s, with the maraschino cherry added to each ring, it had its final canonical look.

Can I use crushed pineapple instead of rings?

Not for the topping. Crushed pineapple will not hold the ring pattern, and it will spill across the surface when the cake is inverted, taking the caramel with it. The whole visual identity of the dish , the ring with the cherry in the middle , is built around the canned ring shape. Save crushed pineapple for a pineapple bread, muffin, or carrot-pineapple cake where it can be folded into the batter.

Can I make this in a Bundt pan?

Technically yes, but you lose the iconic ring pattern. If you do go the Bundt route, use a 10-cup pan, grease it aggressively (butter plus a dusting of brown sugar), arrange pineapple chunks in the bottom of the pan rather than rings, and expect a much more rustic, freeform look. The flavor will be right; the visual will not be. For the canonical version, stick with the skillet or the round cake pan.

Should I invert the cake hot or cold?

Hot. Exactly 10 minutes after the cake comes out of the oven. The caramel is still soft and pourable at that point, the fruit releases cleanly from the skillet, and the topping settles glossily onto the cake. Wait longer than 10 minutes and the caramel begins to set into a hard, glassy layer that bonds the pineapple to the pan; once that happens, half the fruit stays behind when you flip. If you have already missed the window, return the skillet to a 350°F (175°C) oven for 2 to 3 minutes to re-melt the caramel, then flip immediately.

How do I store leftover pineapple upside-down cake?

Covered at room temperature for up to 2 days, or refrigerated for up to 5. Room temperature is preferable; the cold firms the caramel and slightly dries the crumb. For longer storage, wrap individual slices tightly in plastic and freeze for up to 3 months; thaw on the counter for 1 to 2 hours and warm in a 300°F (150°C) oven for 5 to 7 minutes before serving. The cake survives the freezer better than the caramel, but the dish overall holds up.

Final Thoughts

Pineapple upside-down cake is one of those recipes that sits in almost every American kitchen and almost never gets revisited honestly. Most versions are fine. A few are great. The difference comes down to two decisions: canned pineapple over fresh, and the 10-minute inversion window over the longer cool that most recipes suggest.

The cultural anchor is worth holding onto. Mrs. Robert Davis of Norfolk, Virginia, won a national recipe contest in 1925 with a cake she almost certainly built in a cast iron skillet on a wood-fired stove. The version above is the same cake , butter and brown sugar caramel, canned pineapple rings (because that is what the Ginaca machine was inventing the year she was learning to bake), maraschino cherries in every center, a buttermilk batter, and the trust that the flip happens fast.

Bake this for Easter, for a retro dinner party, or for a Sunday afternoon when the kitschy visual is exactly what the table needs. Cut a wedge while it is still warm enough to soften a scoop of vanilla ice cream on top, and remember that you are eating a cake that has held its place on American tables for a century for a reason.

Last update on 2026-08-08 / Affiliate links / Images from Amazon Product Advertising API