Ingredients
- ½ cup butter
- 1 cup packed brown sugar
- 1 (14 ounce) can pineapple slices, drained and juice reserved
- 15 maraschino cherries, or more to taste
- 1 (14 ounce) can crushed pineapple, drained and juice reserved, divided
- 1 (15.25 ounce) package cherry chip cake mix
- 1 cup juice from canned pineapple
- 3 eggs, lightly beaten
- ½ cup melted butter
- 1 ½ fluid ounces rum
Why This Dish Is A Crowd Favorite
Practical Cooking Tips
- Arrange the fruit carefully to create an attractive pattern when flipped.
- Allow the cake to cool slightly before inverting to prevent the topping from sticking.
Step 1
Preheat your oven to 350°F (175°C). Next, take a 9x13-inch cake pan and put half a cup of butter in it. Pop the pan into the oven just long enough for the butter to melt, then carefully take it out and use a brush or spoon to spread the melted butter up the sides of the pan.
Step 2
Sprinkle brown sugar evenly over the melted butter, then arrange pineapple rings on top. Place maraschino cherries in the center of each ring and tuck a few between them for a pretty pattern. You’ll have some crushed pineapple left over—drain half of it really well and use that to fill in any gaps between the rings so the whole bottom is covered.
Step 3
In a large bowl, mix together the cake mix, one cup of pineapple juice, eggs, and half a cup of melted butter. Start beating on low just until everything is combined, then crank it up to medium and beat for about two minutes. Stir in the rum and the reserved crushed pineapple until it’s all mixed through.
Step 4
Pour the batter over your pineapple and sugar layer, spreading it out evenly with a spatula. Bake for 30 to 35 minutes, or until a toothpick poked into the center comes out clean (just be careful not to push the toothpick all the way through to the bottom).
Step 5
Once it’s done, take the cake out of the oven and immediately run a knife around the edges to loosen it from the pan. Let it sit for a few minutes to cool slightly. Then, place a serving plate upside-down on top of the pan, hold them together firmly, and flip it over. Leave the pan on for a couple of minutes before gently lifting it off to reveal your beautiful upside-down cake.

