I can’t resist sharing this glossy crown of caramelized pineapple rings and cherries perched on a moist, brown-sugar-kissed cake mix that becomes an unforgettable centerpiece for every celebration.

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I’m obsessed with this pineapple upside down cake because it pulls summer into a single bite. The glossy fruit and sticky caramel make my sweet tooth sing, but it’s the yellow cake mix that keeps the texture impossibly tender and the maraschino cherries that flash bright, ridiculous joy on top.

It’s dramatic without trying, retro without sounding dated, and sticky in the best possible way. And the scent when it comes out of the oven, yeah, that’s a full-on assault and I always absolutely, shamelessly do not resist.

Pure, unabashed dessert that looks like celebration and tastes exactly like it.

Ingredients

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Yellow cake mix: quick base, sweet and cakey, makes baking easy.
Eggs: they bind the batter and add a bit of richness.
Water: keeps the batter moist, it doesn’t add flavor.
Vegetable oil: keeps cake tender, it’s neutral and reliable.
Basically vanilla extract: warm background note, I always add it.
Melted butter: it’s pure caramely richness for that glossy topping.
Brown sugar: creates sticky caramel layer you’ll want on every slice.
Pineapple slices: juicy rings that brighten each bite with sweet-tart flavor.
Plus maraschino cherries: bright color pops and tiny bursts of sweetness.
Chopped pecans or walnuts: nuts add crunch and toasty depth, optional.

Ingredient Quantities

1 box (15.25 oz) yellow cake mix

3 large eggs

1 cup water

1/3 cup vegetable oil

1 teaspoon vanilla extract (optional, but i like it)

1/4 cup unsalted butter (melted)

3/4 cup packed light brown sugar

1 (20 oz) can pineapple slices, drained

8 to 12 maraschino cherries, stems removed

1/2 cup chopped pecans or walnuts (optional, for crunch)

How to Make this

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1. Preheat oven to 350 F and grease a 9 inch round cake pan or 9×13 if you want a thinner cake, line bottom with parchment if you have it so flipping is easier.

2. Stir together 1/4 cup melted unsalted butter and 3/4 cup packed light brown sugar until smooth, then spread that mixture evenly across the bottom of the prepared pan.

3. Arrange the drained pineapple slices on top of the brown sugar mixture, placing maraschino cherries in the centers and wherever you like between rings, press them down a little so they stick.

4. If using, sprinkle 1/2 cup chopped pecans or walnuts over the pineapple and sugar for extra crunch; don’t overdo it or the nuts will make the top too thick.

5. In a large bowl whisk together 1 box (1
5.25 oz) yellow cake mix, 3 large eggs, 1 cup water, 1/3 cup vegetable oil, and 1 teaspoon vanilla extract until well combined; batter will be slightly thick but smooth, scrape the sides so nothing’s left.

6. Pour the batter gently over the arranged pineapple, spreading carefully so the rings stay in place; tap the pan lightly on the counter to settle the batter and remove air bubbles.

7. Bake in the preheated oven for 35 to 45 minutes for a 9 inch pan, or 30 to 40 minutes for a 9×13, until a toothpick in the center comes out clean and the top is golden brown.

8. Let the cake cool in the pan on a wire rack for 10 to 15 minutes only, no longer or the glaze will harden and stick too much; run a thin knife around the edges to loosen if needed.

9. Place a serving plate upside down over the pan, quickly invert the cake onto the plate and lift the pan off gently; if a few pieces stick, use a small spatula to coax them free, spoon any pan juices back over the cake for shine.

10. Let the cake cool another 10 minutes before slicing so the topping settles, then serve warm or at room temperature, maybe with whipped cream or vanilla ice cream.

Equipment Needed

1. 9-inch round cake pan (or 9×13 if you want a thinner cake)
2. Parchment paper (optional, but makes flipping easier)
3. Small saucepan or microwave-safe bowl to melt 1/4 cup butter
4. Large mixing bowl for the cake batter
5. Whisk (or a fork if you must)
6. Rubber spatula or offset spatula for spreading batter and glaze
7. Can opener and a slotted spoon or tongs to drain and place pineapple slices
8. Measuring cups and measuring spoons
9. Toothpick or cake tester to check doneness
10. Wire cooling rack and oven mitts for safe handling

FAQ

Q: How long do I bake this cake and at what temperature? A: Preheat oven to 350°F. Bake 30 to 35 minutes or until a toothpick in the center comes out with a few moist crumbs. If the top (really the bottom once flipped) is browning too fast, tent with foil the last 5 to 10 minutes.

Q: How do I keep the pineapple and cherries from sticking to the pan when I flip it? A: Make sure you melt the butter and spread it evenly across the pan before sprinkling the brown sugar. Press the pineapple slices into the sugar and add cherries and nuts. Let the cake cool in the pan for 5 to 10 minutes, then invert onto a plate. If it seems stuck, run a thin knife around the edge first.

Q: Can I use fresh pineapple instead of canned? A: Yes, but slice it thin and pat dry so there is not too much extra juice. Fresh pineapple has more moisture and can make the topping runny, so reduce added water by a few tablespoons if needed.

Q: What if I dont want cherries or nuts? A: No problem. The cherries are mostly for looks and a pop of color, so you can leave them out. Nuts add crunch, but skipping them still gives you a classic, delicious cake.

Q: Can I make this ahead of time and how do I store leftovers? A: You can make it a day ahead. Cool completely, cover loosely with foil or plastic wrap, and refrigerate. Bring to room temperature before serving or warm slices briefly in the microwave. Stored in the fridge it lasts 3 to 4 days.

Q: Any quick swaps if I dont have a boxed yellow mix? A: You can use a white or butter cake mix the same way. If you want gluten free, use a GF cake mix and follow the same liquid and egg amounts though baking time might vary slightly.

Pineapple Upside Down Cake Recipe Using Cake Mix Substitutions and Variations

Eggs: 3 large eggs can be swapped for 3/4 cup applesauce (gives moistness but slightly denser texture), or 3 tablespoons flaxseed meal mixed with 9 tablespoons water (vegan option, let sit 5 min), or 1/2 cup plain yogurt for extra tang.
Vegetable oil: use equal amount neutral-flavored melted coconut oil (adds a mild coconut note), or light olive oil, or 1/2 cup unsweetened applesauce to cut fat and make it lighter.
Unsalted butter (for topping): replace with equal melted salted butter if you forgot unsalted, or use browned butter for nuttier flavor, or use 1/4 cup coconut oil for dairy-free.
Pecans or walnuts: swap for chopped almonds, toasted oats for chew, or leave them out entirely if you need nut-free cake.

Pro Tips

– Use parchment under the brown sugar if you can. It makes the flip way easier and you wont lose any of the pretty pineapple rings when you invert it. If you dont have parchment, run a thin knife around the edges while it is still warm so it comes out clean.

– Don’t overdo the nuts. Sprinkle them lightly so you still get caramel glaze seeping through the fruit. If the nuts clump, they can make the topping too thick and the cake wont bake evenly.

– Drain the canned pineapple really well and pat the slices dry with a paper towel. Excess juice makes the brown sugar run and can make the cake soggy instead of gooey and pretty.

– Let it cool briefly but not too long before flipping. If you wait until the sugar hardens the top will stick. Ten to fifteen minutes is usually perfect; it’ll still be warm but the glaze will loosen enough to release.

Pineapple Upside Down Cake Recipe Using Cake Mix

Recipe by Sam Ecclestone

0.0 from 0 votes

I can't resist sharing this glossy crown of caramelized pineapple rings and cherries perched on a moist, brown-sugar-kissed cake mix that becomes an unforgettable centerpiece for every celebration.

Servings

servings

Calories

352

kcal

Equipment: 1. 9-inch round cake pan (or 9×13 if you want a thinner cake)
2. Parchment paper (optional, but makes flipping easier)
3. Small saucepan or microwave-safe bowl to melt 1/4 cup butter
4. Large mixing bowl for the cake batter
5. Whisk (or a fork if you must)
6. Rubber spatula or offset spatula for spreading batter and glaze
7. Can opener and a slotted spoon or tongs to drain and place pineapple slices
8. Measuring cups and measuring spoons
9. Toothpick or cake tester to check doneness
10. Wire cooling rack and oven mitts for safe handling

Ingredients

1 box (15.25 oz) yellow cake mix
3 large eggs
1 cup water
1/3 cup vegetable oil
1 teaspoon vanilla extract (optional, but i like it)
1/4 cup unsalted butter (melted)
3/4 cup packed light brown sugar
1 (20 oz) can pineapple slices, drained
8 to 12 maraschino cherries, stems removed
1/2 cup chopped pecans or walnuts (optional, for crunch)

Directions

Preheat oven to 350 F and grease a 9 inch round cake pan or 9×13 if you want a thinner cake, line bottom with parchment if you have it so flipping is easier.
Stir together 1/4 cup melted unsalted butter and 3/4 cup packed light brown sugar until smooth, then spread that mixture evenly across the bottom of the prepared pan.
Arrange the drained pineapple slices on top of the brown sugar mixture, placing maraschino cherries in the centers and wherever you like between rings, press them down a little so they stick.
If using, sprinkle 1/2 cup chopped pecans or walnuts over the pineapple and sugar for extra crunch; don’t overdo it or the nuts will make the top too thick.
In a large bowl whisk together 1 box (1
25 oz) yellow cake mix, 3 large eggs, 1 cup water, 1/3 cup vegetable oil, and 1 teaspoon vanilla extract until well combined; batter will be slightly thick but smooth, scrape the sides so nothing’s left.
Pour the batter gently over the arranged pineapple, spreading carefully so the rings stay in place; tap the pan lightly on the counter to settle the batter and remove air bubbles.
Bake in the preheated oven for 35 to 45 minutes for a 9 inch pan, or 30 to 40 minutes for a 9×13, until a toothpick in the center comes out clean and the top is golden brown.
Let the cake cool in the pan on a wire rack for 10 to 15 minutes only, no longer or the glaze will harden and stick too much; run a thin knife around the edges to loosen if needed.
Place a serving plate upside down over the pan, quickly invert the cake onto the plate and lift the pan off gently; if a few pieces stick, use a small spatula to coax them free, spoon any pan juices back over the cake for shine.
Let the cake cool another 10 minutes before slicing so the topping settles, then serve warm or at room temperature, maybe with whipped cream or vanilla ice cream.

Notes

Below you’ll find my best estimate of this recipe’s nutrition facts. Treat the numbers as a guide rather than a rule—great food should nourish both body and spirit. Figures are approximate, and the website owner assumes no liability for any inaccuracies in this recipe.