Creamy, juicy, and impossibly nostalgic, this Pineapple Upside-Down Cake is the kind of dessert that turns an ordinary night into a small celebration. With caramelized brown sugar, buttery pineapple rings, and a soft, tender cake on top, every forkful feels comforting and bright. Fun fact: the pineapple was once a symbol of hospitality and luxury, so serving this cake is a sweet way to welcome guests.

This recipe is special because it’s simple to assemble, quick to prepare, and incredibly family-friendly. Kids love placing the cherries and pineapple slices, and adults love how impressive it looks when flipped. If you enjoy fun twists on classic desserts, you might also like my take on mini pineapple upside-down cheesecakes, which use the same flavors in a single-serve format. Get ready to bake something that looks gourmet but is truly easy — you’ll be excited to serve it warm with a scoop of vanilla ice cream.

What is Pineapple Upside-Down Cake?

Why is it called an upside-down cake Why flip a cake after baking Does that seem backwards or brilliant That playful name captures the whole point — the fruit and sugary glaze are arranged in the pan first, the batter goes on top, and once baked the cake is inverted to reveal a glistening, caramelized fruit topping. Rumor has it someone once declared that “the way to a man’s heart is through his stomach,” and this cake is certainly proof that a sticky-sweet, warm dessert can win just about anyone over. Try it and see why families have passed this fun method down for generations.

Why You’ll Love This

• Caramelized fruit top: The brown sugar and butter melt into a glossy, buttery glaze that soaks into the pineapple and drips into the cake for a delicious contrast of textures.
• Budget-friendly and satisfying: Using a boxed cake mix keeps costs low and prep fast while still delivering big flavor — a great option for feeding a crowd without breaking the bank.
• Bright, nostalgic flavors: Pineapple and maraschino cherries add sweet acidity and pops of color that make each slice feel festive and indulgent.

If you like the classic flavor profile but want a slightly different texture, check out this spin on the recipe for another take: the vintage-style pineapple upside-down cake. You’ll be inspired to experiment. Ready to give it a try Grab your pan and let’s bake.

How to Make:

Quick Overview

This Pineapple Upside-Down Cake is easy, reliable, and perfect for bakers of any skill level. You’ll melt butter and brown sugar to create a sticky base, arrange pineapple rings and cherries, pour simple cake batter over the fruit, then bake for about 42 to 48 minutes. The result is a moist cake with a glossy, caramelized fruit topping and a tender crumb. Prep time is about 15 minutes and baking time is 42 to 48 minutes for a total of roughly 60 minutes from start to finish.

Ingredients

1/4 cup unsalted butter, melted in the pan, room temperature before melting
1 cup packed light brown sugar, evenly sprinkled over melted butter
1 can (20 oz) pineapple slices in juice, drained (reserve the juice)
1 jar (6 oz) maraschino cherries, stems removed, drained
1 box Betty Crocker Super Moist yellow cake mix
Vegetable oil and eggs, quantities as called for on the cake mix box
Reserve the measured pineapple juice and add water to equal 1 cup liquid for the cake mix

Directions

1. Preheat oven to 350°F. Place the 13×9-inch pan in the oven to warm and melt the 1/4 cup unsalted butter directly in the pan. Carefully remove the hot pan from the oven.
2. Evenly sprinkle 1 cup packed light brown sugar over the melted butter, spreading it to cover the bottom of the pan.
3. Arrange pineapple slices on top of the brown sugar in a single layer. Place maraschino cherries in the center of each pineapple ring and in the spaces between slices as desired.
4. Measure the reserved pineapple juice and add water as needed to make 1 cup of liquid total. Prepare the Betty Crocker Super Moist yellow cake mix according to the directions on the box, using the pineapple juice mixture in place of the water. Add the oil and eggs as instructed on the box and mix until smooth.
5. Gently pour the prepared batter over the fruit and brown sugar layer, smoothing lightly so it covers evenly without disturbing the pineapple arrangement.
6. Bake on the middle rack for 42–48 minutes, or until a toothpick inserted in the center comes out clean. Watch the cake during the last 5 minutes to avoid overbaking.
7. Immediately upon removing from the oven, run a knife around the edges of the pan to loosen the cake. Place a heatproof serving plate over the pan and carefully invert the pan and plate together so the cake flips out onto the plate.
8. Let the pan sit on the inverted plate for 5 minutes before lifting the pan straight up to reveal the caramelized fruit top. Allow the cake to cool before slicing. Serve warm or at room temperature.

What to Serve With

Vanilla ice cream or whipped cream for a classic pairing
A drizzle of caramel sauce for extra richness
Freshly brewed coffee or a bright citrus tea to balance the sweetness
A light green salad or fruit salad to create a full dessert-after-dinner feel

Top Tips for Perfecting

• Use room-temperature eggs for the cake mix to help the batter rise evenly.
• Drain pineapple well but reserve the juice — it adds flavor and keeps the cake moist.
• For a deeper caramel flavor, lightly toast the brown sugar in the melted butter before arranging fruit.
• If the cake browns too quickly, tent loosely with foil for the last 10 minutes of baking.
• Avoid pouring batter aggressively over the fruit; pour gently and spread carefully to keep the pineapple arrangement intact.

Storing and Reheating Tips

Refrigeration: Store leftover cake covered with plastic wrap or in an airtight container in the refrigerator for up to 4 days.
Freezing: Slice into portions and freeze in an airtight container with parchment between slices for up to 2 months. Thaw in the refrigerator overnight.
Reheating: Warm slices in the microwave for 15–25 seconds or briefly in a 300°F oven for 8–10 minutes to refresh the glaze and soften the cake without drying it out.

FAQs

Can I use fresh pineapple instead of canned
Yes You can use fresh pineapple rings but you may want to sprinkle a little extra brown sugar beneath them because canned pineapple is sweeter from the syrup or juice.

Do I have to use a cake mix
No You can use a homemade yellow cake batter if you prefer The boxed mix keeps the recipe fast and consistent but a homemade batter will also work.

Why did my topping stick to the pan when I inverted it
If the cake cools too long before flipping the sugar can harden and stick Warm the pan slightly by placing it over a warm surface briefly and try again It often helps to run the knife around the edges more thoroughly before flipping.

Can I make this in a round pan instead of 13×9
Yes You can use a round 9-inch pan but baking time may change Start checking for doneness around 35 minutes as depth and surface area differ.

Can I reduce the sugar for a less sweet topping
Yes You can reduce the brown sugar slightly or swap to a less sweet variety but the texture and caramelization may change A modest reduction of 2 to 3 tablespoons is a safe starting point.

Conclusion

This Pineapple Upside-Down Cake is an easy, crowd-pleasing dessert that brings sunny flavor and cozy nostalgia to any table. With a quick prep and straightforward steps, even beginner bakers can serve a stunning, caramelized cake that feels special. If you want to explore another trusted approach to this classic, check out this detailed variation for inspiration: Pineapple Upside Down Cake – Sugar Spun Run. Give this recipe a try, share slices with family, and enjoy the smiles that follow.