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.
📖 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)
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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