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 13×9″ 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?
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.
Cheryl Day’s Treasury of Southern Baking
