Classic Pineapple Upside Down Cake
This classic pineapple upside down cake features a buttery vanilla cake crowned with caramelized pineapple rings and bright maraschino cherries, all held together with a glossy brown sugar glaze. The beauty of this dessert lies in its simplicity, coming together with basic pantry ingredients in just one pan. When you flip the warm cake onto a serving plate, you’ll reveal a stunning golden, caramelized fruit topping that glistens with sweet, buttery goodness.
Equipment
- 10-inch cast iron skillet - or 9x9-inch baking pan or 10-inch round cake pan with 2-inch sides
- Large mixing bowl
- Medium mixing bowl
- Electric hand mixer - or stand mixer
- Measuring cups
- Measuring spoons
- Rubber spatula
- Wire cooling rack
- Large serving plate - for flipping the cake
- Toothpick - for testing doneness
- Oven mitts
- Paper towels - for drying fruit
- Butter knife - or offset spatula for loosening edges
Ingredients
- 0.5 cup unsalted butter - 115g, melted, plus ½ cup (115g) softened to room temperature for the cake
- 0.75 cup light brown sugar - 165g, packed
- 20 oz canned pineapple rings - 565g can, packed in juice, drained, reserve ⅓ cup (80ml) juice
- 10 maraschino cherries - 10-12, patted dry
- 0.5 cup pecans - 60g, chopped (optional)
For the Cake
- 1.5 cups all-purpose flour - 190g
- 1.5 teaspoons baking powder
- 0.25 teaspoon salt
- 0.5 cup unsalted butter - 115g, softened to room temperature
- 0.75 cup granulated sugar - 150g
- 2 large eggs - room temperature
- 1.5 teaspoons pure vanilla extract
- 0.33 cup pineapple juice - 80ml, reserved from canned pineapple
- 0.33 cup whole milk - 80ml, room temperature
Instructions
- Preheat oven to 350°F (175°C) and position rack in the center. If using a cast iron skillet, warm it in the oven during preheating.
- Melt ½ cup butter in your skillet over medium heat on the stovetop or in the oven. Swirl to coat bottom and sides completely.
- Sprinkle ¾ cup brown sugar evenly over the melted butter, pressing gently with the back of a spoon to create an even layer.
- Drain pineapple rings thoroughly, pat dry with paper towels, and reserve ⅓ cup of juice. Pat maraschino cherries dry as well.
- Arrange 7-9 pineapple rings in a single layer over the brown sugar. Cut remaining rings in half to fill gaps around the edges.
- Place one cherry in the center of each pineapple ring. Tuck additional cherries into spaces between rings. Sprinkle with pecans if using.
- In a medium bowl, whisk together flour, baking powder, and salt for 30 seconds to ensure even distribution.
- In a large bowl, beat softened butter and granulated sugar on medium speed for 3-4 minutes until light and fluffy.
- Add eggs one at a time, beating well after each addition. Mix in vanilla extract. The mixture may look slightly curdled.
- Combine reserved pineapple juice and milk in a small measuring cup. Add one-third of the flour mixture to the butter mixture and mix just until combined.
- Add half the juice mixture, then another third of the flour, the remaining juice mixture, and finally the remaining flour. Mix just until no streaks remain.
- Pour batter evenly over the arranged fruit, spreading gently with a spatula without disturbing the pineapple. Tap pan on counter to release air bubbles.
- Bake in preheated oven for 40-50 minutes until a toothpick inserted in the center comes out clean or with a few moist crumbs.
- Remove cake from oven and cool in pan on a wire rack for exactly 10 minutes. Do not exceed this time.
- Run a butter knife around the inside edge of the pan. Place a serving plate upside down on top of the pan.
- Using oven mitts, hold both pan and plate firmly together. In one quick, confident motion, flip both over together.
- Let sit for 2-3 minutes, then carefully lift the pan straight up. If any fruit sticks, replace it with a fork.
- Allow cake to cool for at least 15-20 minutes before slicing. Serve warm for best flavor.
Notes
- Thoroughly dry fruit: Excess moisture from pineapple rings and cherries is the number one cause of soggy cakes. Pat them completely dry with paper towels.
- Use room temperature ingredients: Take butter, eggs, and milk out of the refrigerator 30-60 minutes before baking for a smoother batter with better texture.
- Don't overmix: Mix just until the flour disappears to keep the cake tender. Overmixing develops gluten, creating a tough, dense texture.
- Measure flour correctly: Spoon flour into your measuring cup and level it off with a knife rather than scooping directly from the bag.
- Time the cooling period precisely: Let the cake cool for exactly 10 minutes before flipping. Too short and the cake will fall apart; too long and the topping will stick.
- Flip with confidence: Use a decisive, quick motion when inverting the cake. Hesitation can cause the topping to shift or slide off.
- Make-ahead instructions: Bake up to 24 hours in advance. Cool completely, cover loosely with foil, and store at room temperature. Warm individual slices in the microwave for 15-20 seconds before serving.
- Freezing instructions: Wrap individual slices tightly in plastic wrap, then aluminum foil. Freeze for up to 3 months. Thaw overnight in the refrigerator before reheating.
- Fresh pineapple version: Cut fresh pineapple into ½-inch thick slices. Add ⅓ cup pineapple juice or apple juice to the batter since fresh pineapple doesn't provide reserved juice.
- Bourbon twist: Add 2 tablespoons bourbon to the melted butter and brown sugar mixture before arranging the pineapple for a sophisticated, grown-up version with deeper caramel notes.