how2heroes » Pineapple Upside Down Cake

Dessert & Baked Goods » Pineapple Upside Down Cake

Judy Rosenberg of Rosie's Bakery takes us back a few decades with this ooey-gooey retro masterpiece: Pineapple Upside Down Cake! Judy begins by caramelizing brown sugar & pineapples for the top...or is it the bottom? A thick, rich batter is poured over the caramelized fruit, then baked together until golden. Judy shows us her trick for inverting the cake once it's baked for premium presentation. Be prepared — after taking a bite you may not know which end is up!

Print Recipe

Serves 8

Ingredients

For the Topping

5½ tbsp unsalted butter
½ cup + 1 tbsp light brown sugar
¼ cup dark brown sugar
10 canned, unsweetened pineapple rings
8-10 maraschino cherries

For the Cake

6 tbsp unsalted butter, room temperature
1 cup sugar, divided
2 large eggs, separated
1½ tsp vanilla extract
1 cup all-purpose flour
½ tsp baking soda
½ tsp baking powder
¼ tsp salt
½ cup buttermilk

Special Equipment

8" cast iron skillet

How-to

Make Topping

Melt the butter in the cast iron skillet over low heat. Add both brown sugars and stir until all the lumps are gone
Turn up the heat to medium-high and cook, 2 minutes Tilt the pan back and forth to avoid burning and ensure even cooking
Place the whole pineapple rings in the pan. Slice the remaining rings in half and position around the sides of the pan and add the maraschino cherries to centers of the rings
Remove from heat and set aside

Make Cake

Place a rack in the lower 3rd of the oven and preheat to 375°
Sift flour baking soda, baking powder and salt together in a small bowl
In a standing mixer with the paddle attached, cream together the butter and ¾ cup of sugar on medium speed until light and fluffy
Add the egg yolks and vanilla to the butter mixture and beat until smooth, scraping down the sides at least once 30. Set aside
In a clean bowl, beat egg whites until foamy
Start to gradually add remaining ¼ cup of sugar and beat until whites are at soft peaks. Set aside
With the mixer on low speed add half the dry ingredients to the butter mixture and blend until just incorporated
Add half of the buttermilk and mix on low speed for about 8 seconds. Add remaining flour, then remaining buttermilk. Mix until almost combined
Remove bowl from stand mixer and finish mixing by hand with a rubber spatula
Fold in one-third of the whites into the batter (to loosen the mixture), then fold in the remaining egg whites

Assemble Cake & Bake

Pour the batter over the pineapple and gently spread to distribute. Place the skillet on the sheet pan in the oven and bake until cake is golden and springs back to the touch. A tester inserted into the cake should come out clean, about 30-40 minutes
Let the cake sit for a few minutes, then run an offset spatula around the sides
Invert onto a plate that is slightly larger than the skillet, while the cake is still warm (use oven mitts!)
Slice and serve warm, or at room temperature