This pineapple upside-down cake delivers everything you want from the retro classic—sticky, buttery caramel; glossy, jammy fruit; and a tender, plush crumb—plus a few smart upgrades.
Cookbook author Cheryl Day swaps in deeply flavorful Luxardo cherries for the usual neon maraschinos, bringing a richer, almost winey sweetness that plays off the bright tang of pineapple. And instead of fussing with fresh fruit, this recipe leans on canned pineapple rings (packed in 100% juice) for their consistent shape, reliable juiciness, and picture-perfect finish.
The payoff is in the flip. Once inverted, the brown sugar–butter topping reveals a mosaic of caramelized fruit that glazes the cake as it settles. What you end up with is a dessert that’s unapologetically nostalgic, a little dramatic, and deeply satisfying—no special occasion required.
Pineapple Upside-Down Cake Tips & FAQs
Can I use fresh pineapple instead of canned?
Canned rings are the most reliable choice for flavor and ease, but fresh pineapple will work here if you don’t mind the extra steps. Remember to slice it into thin, even rings, remove the core (a small cookie cutter works well), and blot the slices to avoid excess moisture.
How can I boost the pineapple flavor?
This cake bakes into a plush vanilla crumb with gentle tang from the sour cream, while most of the pineapple flavor lives in the topping. For a more pronounced fruit note, brush about ¼ cup of the reserved pineapple juice over the warm cake right after baking but before inverting. Think of it like adding a soak to a layer cake—the juices seep into the crumb without making it wet, amplifying the pineapple flavor without changing the structure.
Can I use a different pan (like a cast-iron skillet)?
A metal 13x9" pan is the most foolproof option for even cooking and easy release. If you prefer deeper browning on the bottom and sides (and a more rustic look), you can use a 12" cast-iron pan with 2¼" sides. Because cast iron takes a while to heat up, the cake may take longer to bake; rely on visual cues and a toothpick test to ensure the center is baked through.
You can also split the topping and batter between two 8" cake pans. Keep oven temperature the same and start checking for doneness around the 20-minute mark.
How can I make the cake less sweet?
The salt and sour cream do a lot to balance the flavors here, but there are a few things you can do to keep the sweetness in check. First, weigh your ingredients. Second, use canned pineapple in 100% juice, not syrup, for the topping. You can also swap in fresh pineapple for a brighter finish.
If the cake is still too sweet for your liking, you can reduce the sugar in the batter by 2–3 Tbsp. without much sacrifice to the texture.
Is there any substitute for Luxardo cherries?
We love the rich flavor of Luxardo cherries, but they’re not cheap. Thankfully, you have a plethora of options in the cocktail cherry market these days. St. Agrestis makes amaro-soaked cherries with a definitive bitterness, while the cherries from Hotel Starlino, Toschi, and Amarena Fabbri are syrupy sweet with a bright tang from the tart fruit used to make them.
Do I have to use cake flour?
Cake flour produces a softer, more tender crumb with a delicate, melt-in-your-mouth, bakery-style finish. Swapping in all-purpose flour will work, but the cake will be notably denser with a more structured crumb.
A common hack for cake flour is to measure out the same volume of all-purpose flour, then remove 2 Tbsp. per cup, and replace them with 2 Tbsp. cornstarch. This can also work, but the finished texture will still be slightly altered.
This recipe was adapted from ‘Cheryl Day’s Treasury of Southern Baking’ by Cheryl Day. Buy the full book on Amazon or Bookshop.
What you’ll need
Stand Mixer
$400 $280 At Amazon
Luxardo Maraschino Cherries
$24 At Amazon
Metal Baking Pan
$26 At Amazon
Scale
$26 At Amazon
Offset Spatula
$15 At Amazon
Small Saucepan
$155 At Amazon
Microplane Grater
$18 At Amazon
Silicone Spatula
$13 At Amazon
Unbleached and Unenriched Cake Flour
$5 At King Arthur Baking Company
Recipe information
Total Time
1 hour (plus cooling)
Yield
12 Servings
Ingredients
Caramel Topping
1
6
1
1
1
8
Cake and Assembly
2½
1
1
¼
3
1
12
1½
1½
Need to make a substitution?
Preparation
Caramel Topping
Step 1
Place a rack in middle of oven; preheat to 350°. Place a 13x9" metal baking pan by the stove. Cook 1 cup (packed; 200 g) light brown sugar, 6 Tbsp. unsalted butter, 1 Tbsp. vanilla extract, and 1 tsp. Diamond Crystal or ½ tsp. Morton kosher salt in a small saucepan over medium heat, stirring occasionally, until butter is melted and mixture is bubbling, about 5 minutes.
Step 2
Pour caramel into baking pan and, using a heatproof rubber spatula, spread to evenly coat bottom, nudging it into the corners. Arrange slices from one 15-oz. can pineapple slices, drained, patted dry, on top of caramel without overlapping. Place 1 of 8 maraschino cherries (such as Luxardo), stems removed, patted dry, in the center of each pineapple ring. Set pan aside.
Cake and Assembly
Step 3
Whisk 2½ cups (288 g) cake flour, 1 Tbsp. baking powder, 1 Tbsp. Diamond Crystal or 1¾ tsp. Morton kosher salt, and ¼ tsp. ground mace or freshly grated nutmeg in a medium bowl. Whisk 3 large eggs, room temperature, and 1 Tbsp. vanilla extract in a small bowl.
Step 4
Beat 12 Tbsp. (1½ sticks) unsalted butter, room temperature, and 1½ cups (300 g) granulated sugar in the bowl of a stand mixer fitted with the paddle attachment on medium-high speed until light and fluffy, about 4 minutes. Reduce speed to medium and add egg mixture in 4 additions, beating 30 seconds after each addition before adding more and scraping down bowl with a rubber spatula as needed.
Step 5
Reduce mixer speed to low and add dry ingredients in 3 additions, alternating with 1½ cups sour cream in 2 additions, mixing 30 seconds after each addition. Fold batter a few times with a clean spatula, scraping down sides to make sure everything is well mixed. Scrape batter into reserved pan and smooth surface.
Step 6
Bake cake until golden and a tester inserted into the center comes out clean, 40–50 minutes. Transfer pan to a wire rack; let cake cool in pan 15 minutes. Run an offset spatula along edges of cake to loosen. Set a large platter over pan and flip over to release cake; carefully remove pan. If any fruit or cake sticks to pan, scrape it off and press back onto top of cake. Serve warm or room temperature.
Do ahead: Cake can be baked 3 days ahead. Store airtight at room temperature.
Editor’s note: This pineapple upside-down cake recipe was first printed online in October 2021; it has been edited for clarity and style. Head this way for more of our favorite pineapple recipes →
Buy it on Amazon or Bookshop.org