Pineapple Upside Down Cake For a Crowd Recipe
Soft, light vanilla yellow cake soaked with caramelized brown sugar, butter, pineapple slices and cherries.
How to Make the Best Pineapple Upside Down Cake For a Crowd
There’s nothing quite like a slice of pineapple upside down cake to bring back nostalgic memories of summer gatherings and celebration dinners. This pineapple upside down cake for a crowd is a showstopper dessert that looks impressive when inverted, revealing a beautiful golden display of caramelized pineapple rings and bright red marachino cherries on top.
This recipe is specifically designed to feed a crowd—baked in a half-sheet pan, it yields 20 generous slices perfect for potlucks, family reunions, or special occasions. The foundation is a soft, tender vanilla cake with a delicate crumb, enriched with sour cream and milk for incredible moisture. What makes this dessert truly special is the buttery caramel base studded with pineapple slices and cherries that becomes the gorgeous topping when the cake is inverted onto a serving platter.
The best part? This cake is straightforward to make despite its impressive appearance. Just make sure to let it cool slightly before inverting—rushing this step can result in the caramel running off the sides. Once properly cooled and flipped, you’ll have a stunning dessert that’s sure to impress everyone at the table.
Pineapple Upside Down Cake For a Crowd
Soft, light vanilla yellow cake soaked with caramelized brown sugar, butter, pineapple slices and cherries.
Ingredients
For the Pan
For the Cake
Instructions
Prepare the Pan
- Preheat oven to 350°F.
- Melt 2 sticks of unsalted butter and pour into a 12 x 18 x 3 pan. Spread evenly over the pan.
- Sprinkle the brown sugar evenly over the butter.
- Evenly distribute the sliced pineapple (5 rows of 4) in the pan with a cherry in the middle of each ring. Set aside.
Make the Cake Batter
- In a medium bowl, whisk together all-purpose flour, baking soda, and salt. Set aside.
- In a standing mixer fitted with the paddle attachment or in a large bowl with a hand mixer, beat the butter on medium-high speed until pale and fluffy. Scrape down the bowl if needed and add the sugar.
- Beat on medium-high until incorporated, about 1 minute.
- With the mixer on low, add eggs one at a time. Add vanilla and sour cream. Scrape down the bowl if needed and increase speed to medium, mix for 1 minute.
- Working in two batches with the mixer on low, add 1/2 the flour mixture followed by half the milk. Mix until incorporated and repeat with remaining ingredients. Scrape down bowl if needed, increase speed to medium and mix until smooth and incorporated (about 1 minute).
Bake
- Pour batter over prepared pan and spread evenly with spatula. Some of the butter may pool up around the sides—if this happens, spread more cake batter in that area. The edges of the cake should be buttery and gooey.
- Bake on the middle rack in the preheated oven for 45 minutes. The 'top' of the cake will brown slightly during baking and edges may crisp just a touch from the butter and brown sugar.
- Let cool 20 to 30 minutes before serving.
- To serve, turn cake over onto a large cutting board or serving platter. If the cake is turned over before the butter and brown sugar cool and thicken, it will leak all over the countertop.
Notes
- This recipe yields 20 generous slices, making it perfect for parties and gatherings.
- The caramelized topping is best when the cake cools slightly before inverting—don't rush this step!