This light and airy Pineapple Upside Down Cake, made with a box of cake mix, is a simple yet impressive dessert. It has the classic caramelized brown sugar top, canned pineapple rings, and a soft and tender cake.
I am absolutely swooning over this Pineapple Upside Down Cake, made with a box of cake mix. The caramelized brown sugar topping pairs beautifully with the tender pineapple and fluffy yellow cake.
It’s baked in a single layer 9-inch round pan, and slices into six portions, each topped with a whole pineapple ring. Best of all, it keeps things simple by using a box of Jiffy yellow cake mix. The mix is 9 ounces, so it’s smaller than a standard sized cake mix, and it fits perfectly in one round pan.
The recipe came from a 1980s spiral-bound recipe book. The recipe submitter notes that you can double the recipe and bake it in a 13×9-inch pan if you’d like a larger cake.
I’m always a little nervous about getting upside down cakes to release cleanly, but this one flipped right out onto the serving platter. I topped it with a dollop of homemade whipped cream, which I heartily recommend!
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Why You’ll Love This Cake
- It bakes in a single layer 9-inch round cake pan (here’s the one I have), so you get just the right amount without a lot of leftovers.
- The brown sugar and butter melt into a thin caramel-like sauce that seeps into the cake and coats the pineapple.
- It’s simple. Make the topping, mix the cake, pour it in the pan, and bake. I particularly love that it’s made with Jiffy cake mix, which I found for less than $1 at my local grocery store. The cake mix only calls for an egg and water (no need to add oil).
What You’ll Need
- You want a single layer cake mix (9 oz) here. Jiffy is the most popular brand.
- The egg is for mixing up the cake mix. You’ll also need water.
- The maraschino cherries are optional, but I love the pop of color that they add to the cake. If you don’t have them, leave them out, or substitute a pecan half or chopped pecans instead.
- Pineapple rings make for a really beautiful cake, but you can also substitute crushed pineapple (drained well).
How to Make Pineapple Upside Down Cake with Boxed Cake Mix
- Melt butter in a 9-inch cake pan. Top with brown sugar.
- Top with pineapple rings and maraschino cherries.
- Mix a box of single layer cake mix (Jiffy just calls for an egg and water).
- Pour cake mix over the top of the pineapple rings and bake for 30 minutes at 350°F. Remove from the oven and invert immediately onto a serving platter.
Tips and Tricks for Making the Cake
- Drain the pineapple rings in a colander before adding them to the brown sugar mixture. If you’re using crushed pineapple, press it to remove the juice.
- You may need to squeeze the pineapple rings into the pan (I put 6 around the edges and 1 in the middle). Overlap a bit if you need to. They won’t look so squeezed when you invert the cake though. Here’s the 9-inch pan that I used.
- Run a butter knife along the edges of the pan before inverting it, and do so right after it gets out of the oven. This ensures it’ll release easily.
If you love upside down cakes, don’t miss my Easy Rhubarb Upside Down Cake!
📖 Recipe
Pineapple Upside Down Cake with Boxed Cake Mix
Ingredients
- ⅓ cup butter
- ½ cup brown sugar
- 1 can (20 oz) pineapple slices, drained
- 7 –8 maraschino cherries optional
- 1 box (9 oz) Jiffy yellow cake mix (made according to package directions)
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Instructions
- Preheat oven to 350°F. Grease a 9-inch round cake pan on the bottom and sides.
- Place ⅓ cup butter in the cake pan and place in the oven to melt.
- Meanwhile, prepare 1 box (9 oz) Jiffy yellow cake mix according to package directions. (Jiffy mix calls for an egg and water.)
- Remove the pan from the oven (butter should be melted). Sprinkle ½ cup brown sugar over the top of the butter. Place the pineapple slices in a decorative pattern on top of the brown sugar (I squeezed 7 pineapple rings into the 9-inch round pan). Place a maraschino cherry inside each pineapple ring, if desired.
- Pour the cake batter over the top.
- Bake for 28–32 minutes for a 9-inch round pan, or until a toothpick inserted into the cake comes out clean or with dry crumbs.
- When you remove the cake from the oven, run a knife along the edges of the pan to loosen the cake gently, then immediately turn the cake upside down onto a serving plate. The brown sugar mixture will run down the sides of the cake.
- Serve warm, or let cool before serving. Either way, a dollop of whipped cream on top is an excellent idea.
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