Pineapple upside down cake is a nostalgic dessert that always reminds me of family gatherings and festive dinners. With its glossy caramelized pineapple rings and pops of maraschino cherries, this cake is as beautiful as it is delicious. I love that this version uses a box cake mix—it saves time while still delivering that moist, buttery, tropical flavor everyone craves. Whether I’m baking it for a holiday, a barbecue, or just because I’m craving something sweet, this cake never disappoints.
Why You’ll Love This Recipe
I love how simple and foolproof this pineapple upside down cake is. It looks like I spent hours in the kitchen, but really, it comes together in minutes. The combination of sweet caramelized fruit and soft yellow cake is irresistible. Plus, using a Bundt pan gives it that stunning presentation perfect for holidays or special occasions. It’s a dessert that’s easy enough for a weekday treat yet elegant enough for the Thanksgiving or Christmas dessert table.
Ingredients
(Tip: You’ll find the full list of Ingredients and measurements in the recipe card below.)
1 box yellow cake mix
1 stick butter, halved and melted
¼ cup brown sugar
3 eggs
20 oz can crushed pineapple in 100% juice (or blended tidbits)
1 can pineapple rings
1 small jar maraschino cherries
Directions
Preheat the oven to 350°F.
Pour half of the melted butter into your Bundt pan (or any cake pan) and brush it along the bottom and sides.
Sprinkle the brown sugar evenly over the butter.
Arrange pineapple rings on the bottom and place a maraschino cherry in the center of each.
In a mixing bowl, combine the cake mix, eggs, crushed pineapple (including juice), and the remaining melted butter. Beat on medium for 1 minute, then on high for another minute.
Pour the batter evenly over the fruit layer.
Bake for about 40 minutes, or until a toothpick inserted in the center comes out clean.
Let the cake cool for at least 15 minutes before carefully inverting it onto a serving platter.
Serve warm or at room temperature.
Servings and Timing
This recipe makes about 12 servings. The total time is around 55 minutes—10 minutes for prep and 40–45 minutes for baking, plus cooling time before serving.
Variations
Add Coconut: I sometimes sprinkle sweetened shredded coconut over the pineapple rings before adding the batter for a tropical touch.
Use Different Fruits: Fresh raspberries or slices of kiwi work beautifully in place of cherries.
Try Other Cake Mixes: A pineapple or coconut-flavored cake mix gives this dessert extra depth.
Add a Rum Twist: For adults, I occasionally add a splash of rum extract to the batter for a warm, spiced flavor.
Make Minis: I love baking this recipe in muffin tins for adorable, individual servings.
Storage/Reheating
I store leftovers covered at room temperature for up to 2 days, or in the refrigerator for up to 5 days. To reheat, I warm slices in the microwave for about 15–20 seconds. The caramel topping softens again, making the cake taste just like it’s fresh from the oven. If I’m planning ahead, I sometimes wrap slices in plastic wrap and freeze them for up to 3 months—just thaw in the fridge overnight before serving.
FAQs
How do I keep the pineapple topping from sticking to the pan?
I always make sure to generously coat the pan with melted butter and sprinkle the brown sugar evenly before arranging the pineapple. This creates a caramel layer that releases easily when the cake is inverted.
Can I use fresh pineapple instead of canned?
Yes! I often use fresh pineapple for a slightly tangier flavor. I just slice it thinly so it bakes evenly and still softens beautifully.
Why did my cake fall after baking?
This can happen if it’s underbaked or overmixed. I make sure to test it with a toothpick before removing it from the oven and mix only until the batter is smooth.
Can I make this ahead of time?
Definitely. I like to bake it the day before serving. Once it cools, I cover it tightly. The flavors actually deepen overnight, making it even better the next day.
Can I use a different type of pan?
Yes, I’ve made this in round and rectangular pans too. Just adjust the baking time—start checking at 30 minutes for shallower pans.
Conclusion
This pineapple upside down cake is one of my all-time favorite desserts to make. It’s classic, simple, and stunning every time I flip it out of the pan. The mix of caramelized pineapple, tender cake, and buttery brown sugar is pure comfort in every bite. Whether I’m baking it for the holidays, a special gathering, or just a quiet evening at home, this cake always brings a little joy (and a lot of compliments) to the table.
Pineapple Upside Down Cake is a nostalgic dessert featuring caramelized pineapple rings and cherries atop a moist yellow cake, baked in a Bundt or round pan and flipped for a stunning presentation.
Ingredients
1 box yellow cake mix
1 stick (8 tbsp) butter, halved & melted
¼ cup brown sugar
3 eggs
20 oz can crushed pineapple in 100% juice (or blended tidbits)
1 can pineapple rings (for the top)
1 small jar maraschino cherries
Instructions
Preheat the oven to 350 °F (175 °C).
Pour half the melted butter into your prepared Bundt pan (or 9‑inch round). Brush the butter along the bottom and sides.
Sprinkle the brown sugar evenly over the melted butter.
Arrange pineapple rings on the butter‑sugar layer and place a maraschino cherry in the center of each ring.
In a mixing bowl, combine the cake mix, eggs, crushed pineapple (with juice), and remaining melted butter. Beat on medium for 1 minute, then on high for 1 minute.
Pour the batter evenly over the pineapple layer.
Bake for about 40 minutes or until a toothpick inserted into the center comes out clean.
Let the cake cool for at least 15 minutes, then carefully invert onto a serving platter so the pineapple rings are now on top.
Serve warm or at room temperature.
Notes
Use shredded coconut or chopped nuts between the pineapple layer and batter for a tropical twist.
Substitute half the eggs with applesauce or mashed banana for a lighter texture.
Try an alternative cake mix flavor (such as coconut or pineapple) to enhance the theme.
For a rum‑flavored version, add 1 teaspoon of rum extract to the batter.
When using fresh pineapple, cut thin slices and pat dry to avoid excess moisture; excess liquid can make the cake soggy. :contentReference[oaicite:0]{index=0}
