Pineapple Upside-Down Cake is a warm, caramelized, juicy classic that feels like a hug in dessert form — sweet, buttery, and bright with pineapple. This easy-to-make cake turns simple pantry ingredients into something special: a brown sugar glaze, tender yellow cake, and glossy pineapple rings with cherries that always look festive. Fun fact: the first upside-down cakes became popular in the early 1900s when home bakers used canned fruit and brown sugar for an elegant yet simple finish.
This recipe is perfect for busy weeknights or potlucks because it comes together quickly and reliably. It’s family-friendly, kid-approved, and a great way to use pantry staples. If you enjoy retro comfort desserts, you might also like our classic pineapple upside-down cake guide with extra tips on presentation. Get ready for an effortless dessert that’s both impressive and comforting — you’re going to love making this.
What is Pineapple Upside-Down Cake?
Why is it called upside-down? Because the prettiest part — the pineapple and brown sugar glaze — is placed in the bottom of the pan before pouring the cake batter on top. After baking, you flip the pan so the fruit becomes the cake’s crown. Sounds backward, right? But isn’t that the fun of it? Who wouldn’t want the crown on top? There’s a playful kitchen rumor that flipping a warm, fragrant cake is the way to a man’s heart is through his stomach. So grab your spatula and channel that vintage charm — I dare you not to smile when that caramelized pineapple peeks out.
Why You’ll Love This
- Sweet, buttery caramelized topping: The brown sugar melts into the butter and forms a glossy, slightly sticky layer that soaks into the cake edges for irresistible bites.
- Budget-friendly and pantry-smart: This dessert uses one box of cake mix and a few canned items, which keeps costs low while feeding a crowd. Making it at home saves money and tastes fresher than store-bought alternatives.
- Bright, tropical flavor with a nostalgic look: Pineapple rings and cherries give that classic, cheerful presentation — perfect for celebrations or casual dinners.
Compared to other fruit-forward cakes, like our tropical twist in the Hawaiian carrot pineapple cake, this version is far quicker and leans into a caramelized, glossy finish. Ready to try it? Let’s bake!
How to Make
Quick Overview
This Pineapple Upside-Down Cake is straightforward: prepare the brown sugar glaze in the pan, arrange fruit, pour an easy cake mix batter over top, and bake. Prep is simple and clean-up is minimal. Expect about 15 minutes active prep and 42–48 minutes baking, for roughly 60 minutes total. The cake bakes to a tender crumb with a moist interior and a slightly crisp, caramelized fruit topping.
Ingredients
- 1/4 cup unsalted butter, melted in the pan (see directions)
- 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, amount as called for on the cake mix box (use the box’s specified quantity)
- Eggs, quantity as called for on the cake mix box (use room temperature eggs if possible)
Directions
- Preheat the oven to 350°F. Place the 1/4 cup unsalted butter in a 13×9-inch baking pan and put the pan in the oven just long enough for the butter to melt — about 3 to 5 minutes. Carefully remove the hot pan from the oven and tilt to coat the bottom with melted butter. Sprinkle 1 cup packed light brown sugar evenly over the melted butter so the sugar covers the entire bottom of the pan.
- Arrange the drained pineapple slices on top of the brown sugar in a single even layer. Place a maraschino cherry in the center of each pineapple ring, and tuck remaining cherries in between slices or wherever you like for a fun pattern. Take a step back — it already looks delightful.
- Measure the reserved pineapple juice. Add enough water to the reserved juice to equal 1 cup of liquid total. In a mixing bowl, prepare the Betty Crocker Super Moist yellow cake mix according to box directions, substituting the juice-and-water mixture for the water called for on the box. Add the vegetable oil and eggs as directed on the box. Mix until the batter is smooth but don’t overmix.
- Gently pour or spoon the cake batter over the fruit and sugar layer, spreading carefully so the fruit stays in place. Smooth the top lightly with a spatula. Place the pan in the preheated oven and bake for 42–48 minutes, or until a toothpick inserted into the center comes out clean or with a few moist crumbs.
- When baking is complete, remove the pan from the oven and immediately run a knife around the edges to loosen the cake from the pan. Place a heatproof serving plate over the pan and carefully invert the pan and plate together so the cake flips onto the plate with the fruit on top. Let the inverted pan sit on the plate for 5 minutes before lifting the pan to reveal the glossy top.
- Allow the cake to cool to warm or room temperature before slicing. Serve slightly warm for the best caramel flavor or at room temperature if serving later.
What to Serve With
- A dollop of whipped cream or a scoop of vanilla ice cream to balance the caramel sweetness.
- Freshly brewed coffee or a mild black tea for a comforting pairing.
- A citrusy salad with arugula, orange segments, and a light vinaigrette for contrast.
- Grilled ham or roasted pork for a full retro dinner menu — the sweet pineapple pairs beautifully with savory mains.
Top Tips for Perfecting
- Use room-temperature eggs for a smoother batter and better rise.
- Reserve and measure the pineapple juice carefully — it adds flavor to the cake and replaces water called for on the box.
- Don’t overmix the cake batter; mix just until combined for a tender crumb.
- If your pan seems to bubble over, place a sheet pan underneath to catch any drips.
- For a deeper caramel, use dark brown sugar instead of light, but the flavor will be stronger.
- Avoid flipping the cake while it’s too hot or too cold; 5 minutes after removing it from the oven gives the caramel time to settle so it unmolds cleanly.
Storing and Reheating Tips
- Refrigeration: Store leftover cake covered in the refrigerator for up to 4 days. Keep it in an airtight container or wrapped tightly with plastic wrap.
- Freezing: Slice the cake into portions and freeze in airtight containers or wrapped tightly for up to 2 months. Thaw in the refrigerator overnight.
- Reheating: Warm individual slices in the microwave for 15–20 seconds, or place on a baking sheet and warm in a 325°F oven for 8–10 minutes to revive the caramelized top.
FAQs
Can I make this cake with fresh pineapple instead of canned?
Yes, you can use fresh pineapple rings. Lightly caramelize them in a skillet with the brown sugar and butter before arranging in the pan. Fresh pineapple will add extra brightness but may release more juice, so watch the baking time.
What if I don’t have a 13×9-inch pan?
A similar-sized pan will work; if smaller, the cake will be thicker and require a longer baking time. Reduce depth variations by checking doneness with a toothpick starting at the minimum baking time.
Can I make this recipe without maraschino cherries?
Absolutely. Omit the cherries or replace them with halved fresh cherries or berries for a different look and flavor.
How do I prevent the sugar from burning?
Ensure your oven temperature is accurate and don’t overbake. If using darker sugar, monitor closely as it browns faster. Using a sheet pan underneath the cake prevents spills from burning on the oven floor.
Can I make this gluten-free?
Yes, swap the cake mix for a gluten-free yellow cake mix and follow package instructions, using the pineapple juice mix in place of water.
Conclusion
This Pineapple Upside-Down Cake is a timeless, crowd-pleasing dessert that’s quick to prepare, budget-friendly, and endlessly charming. With a buttery brown sugar glaze, tender cake, and bright pineapple rings, it’s an easy win for family dinners and gatherings. For another take on this beloved classic and more detailed tips, check out Sugar Spun Run’s pineapple upside-down cake recipe. Give this recipe a try — it’s simple to make and delightful to share.
Pineapple Upside-Down Cake
Equipment
- 13x9-inch baking pan
- Mixing Bowl
Ingredients
Ingredients
- 1/4 cup unsalted butter melted in the pan
- 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
- as called for cup vegetable oil use the box’s specified quantity
- as called for number eggs use room temperature eggs if possible
Instructions
- Preheat the oven to 350°F. Place the 1/4 cup unsalted butter in a 13x9-inch baking pan and put the pan in the oven just long enough for the butter to melt — about 3 to 5 minutes. Carefully remove the hot pan from the oven and tilt to coat the bottom with melted butter. Sprinkle 1 cup packed light brown sugar evenly over the melted butter so the sugar covers the entire bottom of the pan.
- Arrange the drained pineapple slices on top of the brown sugar in a single even layer. Place a maraschino cherry in the center of each pineapple ring, and tuck remaining cherries in between slices or wherever you like for a fun pattern.
- Measure the reserved pineapple juice. Add enough water to the reserved juice to equal 1 cup of liquid total. In a mixing bowl, prepare the Betty Crocker Super Moist yellow cake mix according to box directions, substituting the juice-and-water mixture for the water called for on the box. Add the vegetable oil and eggs as directed on the box. Mix until the batter is smooth but don’t overmix.
- Gently pour or spoon the cake batter over the fruit and sugar layer, spreading carefully so the fruit stays in place. Smooth the top lightly with a spatula. Place the pan in the preheated oven and bake for 42–48 minutes, or until a toothpick inserted into the center comes out clean or with a few moist crumbs.
- When baking is complete, remove the pan from the oven and immediately run a knife around the edges to loosen the cake from the pan. Place a heatproof serving plate over the pan and carefully invert the pan and plate together so the cake flips onto the plate with the fruit on top. Let the inverted pan sit on the plate for 5 minutes before lifting the pan to reveal the glossy top.
- Allow the cake to cool to warm or room temperature before slicing. Serve slightly warm for the best caramel flavor or at room temperature if serving later.