Pineapple Upside Down Cake — Box Mix Birthday Cake That Looks Like You Tried
The Birthday Cake I Make Every Year — Box Mix and All
Pineapple upside down cake is Jason’s favorite, and it has been his birthday cake almost every year of our marriage. I make it from a box, and I will not apologize for it. A pineapple supreme cake mix, a stick of butter, a cup of packed brown sugar, a can of pineapple rings, and a jar of maraschino cherries turn into a showstopper cake in about 45 minutes. The flip is the only scary part, and I do it on camera every time because I’m either crazy or brave.
🍰 This one’s in my collection of desserts for a crowd — the ones that travel well and feed a lot of people.
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Watch me make this pineapple upside down cake from start to finish — or scroll down for the full printable recipe card.
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Pineapple Upside Down Cake
Start CookingIngredients
- 1 box (15.25 oz) pineapple cake mix I use Duncan Hines Pineapple Supreme cake mix
- 1 cup water
- ½ cup avocado oil or vegetable oil
- 3 large eggs
- ½ cup salted butter 1 stick, melted
- 1 cup brown sugar packed
- 1 can (20 oz) pineapple rings in juice, drained
- ½ jar (about 1/2 cup) maraschino cherries halved
Don’t Want to Plan? I Got You.Every Saturday I share a full week of dinners, sides, and a dessert — with the grocery list already done. Come grab this week’s Weekly Meal Plans!Method Start Cooking
- Preheat oven to 350°F.
- Pour one stick of melted butter into a 9×13 pan. Tilt the pan to spread butter evenly across the bottom.
- Sprinkle 1 cup packed brown sugar evenly over the melted butter. Use the back of a spoon to gently spread and pack the sugar into the butter.
- Drain the can of pineapple rings. Arrange pineapple rings in a single layer over the brown sugar — about 9 to 10 rings will fit a 9×13 pan.
- Place half a maraschino cherry, cut side up, in the center of each pineapple ring.
- In a large mixing bowl, combine the cake mix, 1 cup water, ½ cup avocado oil, and 3 eggs. Beat with an electric mixer on low for 30 seconds, then on medium for 2 minutes until smooth.
- Gently pour the cake batter over the pineapple and cherry layer, spreading evenly with a spatula to cover all the pineapple.
- Bake at 350°F for 32 to 36 minutes, until a toothpick inserted in the center comes out clean.
- Remove from oven and let cool for 30 minutes. Run a knife around the edges of the pan to loosen.
- Place a serving platter upside down on top of the pan. Holding both firmly together, flip the pan and platter over in one motion. Lift the pan straight up — the cake should release cleanly.
- Let cool another 15 to 20 minutes before slicing. Cut into 12 to 15 squares and serve.
Nutrition
Video
Notes
Four Weeks of Family-Friendly FoodWhen people gather, I cook. Four weeks of the dinners my crowd asks for — planned, tested, and shopped for. Come see what’s in the cookbook →Why This Pineapple Upside Down Cake Works
Pineapple upside down cake has a reputation for being fussy because of the flip, but it’s actually one of the easiest celebration cakes I make. There is no frosting to whip, no piping, no layers to stack. The decoration is built into the bottom of the pan before the batter even goes in — melted butter, brown sugar, pineapple rings, cherries — and when you turn it out at the end, it looks like you spent the whole day on it.
Using a box mix is the move. I use Duncan Hines Pineapple Supreme cake mix because it’s made with real pineapple juice, so the cake itself carries the same flavor as the topping. The mix calls for water, oil, and three eggs — stuff you already have. Five minutes of stirring, pour it over the assembled pan, bake. That is the whole job.
Upside down cakes go back hundreds of years — long before home ovens, when people baked “skillet cakes” over open fires by lining the pan with fruit and pouring batter on top. The pineapple version got its start when the Hawaiian Pineapple Company ran a recipe contest in 1925 and got flooded with submissions for upside down cake. The Kitchn has a great write-up on how this cake earned its retro charm. Mine sits on a pineapple-shaped serving tray my mama thrifted for me years and years ago — I use it every single time I make this cake.
A Few Things That Make Pineapple Upside Down Cake Even Easier
- Melt the butter directly in my 9x13 Pyrex in the oven while it preheats. Stick the stick of butter in the pan, slide the pan into a cold oven, set it to 350°F, and by the time the oven is up to temp, the butter is melted and the pan is one step closer. One less bowl to wash.
- Pack the brown sugar firmly before sprinkling. Loose brown sugar gives you a thin, patchy glaze. Pack it into a 1-cup measure with the back of a spoon, then crumble it across the butter evenly. That tight pack is what makes the caramelized top so glossy.
- Drain the pineapple rings well, but save the juice. Too much juice in the pan and the glaze gets soupy under the cake. Tip the can over the sink and let it drain a good 30 seconds. The saved juice is great in a Shirley Temple for kid birthday parties, or you can use it instead of the water the cake mix calls for if you want extra pineapple punch.
- Cherry halves, cut side down. Whole cherries roll, and they look puffy on top when the cake is flipped. Halved cherries sit flat in the center of each pineapple ring with the cut side facing down into the pan — when you flip the cake, the rounded side of the cherry is what you see, glossy and perfect.
- Let it cool 30 minutes — then FLIP. Too soon and the cake is still soft enough to break apart in the flip. Too long and the caramelized sugar starts to harden and stick to the pan. Ten minutes is the sweet spot: still warm, structurally sound, glaze still glossy. Run a knife around the edges, put your platter on top, and commit. The flip is faster than thinking about it.
Pineapple Upside Down Cake FAQ — The Questions I Get Every Time
What temperature and how long do I bake pineapple upside down cake?
Bake at 350°F for 32 to 36 minutes, until a toothpick inserted in the center comes out clean. Mine took 36 minutes the day I made it for the video. If your oven runs hot, start checking at 32. The cake should look golden and pull just slightly away from the edges of the pan when it’s done.
Can I use a regular yellow cake mix instead of pineapple supreme?
Yes. A yellow cake mix works perfectly fine and tastes great with the pineapple topping. The pineapple supreme just adds an extra layer of pineapple flavor in the cake itself, so you get pineapple top and pineapple all the way through. If pineapple supreme is sold out at your store, yellow is the next best swap. White cake mix works too but the color is paler.
Can I make pineapple upside down cake from scratch?
Of course. A simple butter cake batter works beautifully — it’s actually the classic preparation. I use a box mix because my life is too busy not to take the shortcut, and the result on Jason’s birthday plate is the same one he loved last year. If you want to bake from scratch, swap the cake mix step for any standard 9×13 yellow cake recipe and proceed with the butter, brown sugar, pineapple, and cherry assembly exactly the same way.
How long does pineapple upside down cake stay fresh?
Three days, covered tightly with plastic wrap on the counter. The pineapple topping keeps the cake moist longer than most cakes — day-two pineapple upside down cake is honestly just as good as day-one. After three days the cake starts to dry out around the edges. If you need to keep it longer than that, refrigerate it (it’ll keep 5 days in the fridge) and let it come back to room temperature before serving.
Can I freeze pineapple upside down cake?
You can. Wrap individual slices tightly in plastic wrap, then foil, and freeze up to 2 months. Thaw on the counter for a couple of hours. The texture stays good — the only thing I’d watch for is the pineapple getting a little more watery after freezing, so blot any extra moisture off the top with a paper towel before serving. For a fresh-baked celebration cake, though, I’d just make it the day of.
Why did my pineapple upside down cake stick to the pan?
Two most common culprits. First, the cake cooled too long before flipping — the caramelized sugar hardens as it cools and welds to the pan. Flip at 30 minutes. Second, the butter wasn’t fully covering the bottom before the brown sugar went down. Tilt the pan to make sure the melted butter reaches all four corners. A little sticking is normal in one or two spots (mine usually has a small spot or two), but the whole-bottom stick means it sat too long.
How many people does pineapple upside down cake serve?
A 9×13 pineapple upside down cake serves 12 to 15 people cut into squares, which is plenty for a family birthday or a small gathering. For bigger crowds (church potluck, school event, large birthday party), make two pans — they bake at the same time on the same rack and the assembly only takes about five extra minutes per pan.
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Ingredients
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More Crowd-Pleasing Cake Recipes You’ll Love
- Easiest Most Delicious Coconut Cake — another box-mix masterpiece, soaked in cream of coconut and frosted in clouds of whipped topping.
- Easy Box Cake for a Crowd — my hack for turning any box mix into a 9×13 sheet cake everyone fights over.
- Texas Sheet Cake — the warm chocolate sheet cake that disappears in five minutes flat at every potluck.
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Pineapple Upside Down Cake — About Stephanie’s Recipes
Stephanie Longstreth is the home cook, mom, and storyteller behind StephanieCooksForACrowd.com. She cooks for a family of seven in Florida — five kids, two cats, and one husband who appreciates a good meal. Four of her children came home through adoption, and family stories are woven into everything she makes and shares. Find her crowd-friendly recipes, weekly meal plans, and real family life on TikTok, Instagram, YouTube, and Pinterest @stephaniecooksforacrowd.