Grandma has been making pineapple upside-down cake for decades. It’s a family favorite and happens to be Grandpa’s go-to dessert.
This classic has been refined over the years and now includes a small “secret” boost: almond extract. If you prefer, swap in vanilla extract. Either way you’ll get a simple buttery cake that bakes up moist and gooey, topped with caramelized pineapple slices and cherries.
It only takes about 10 minutes to prepare, uses easy-to-find ingredients, and delivers an impressive presentation and delicious flavor. This homemade pineapple upside-down cake is perfect year-round and especially delightful in summer.
Why you’ll love it:
- Signature caramelized topping. The pineapple juices and brown sugar meld into the cake for a sticky, delicious topping.
- Quick prep. Ready to assemble in about 10 minutes.
- Great for sharing. Ideal for barbecues, parties, and holiday gatherings.
Pineapple Upside Down Cake Ingredients
- Unsalted butter, divided (1 cup): Half melts with brown sugar for a glossy caramel; the rest is creamed into the batter for tenderness.
- Packed light brown sugar, divided (1½ cups): Creates the rich caramel topping and sweetens the batter.
- Pineapple rings in juice (1, 20-ounce can): Drain and reserve ½ cup of juice. Pat the rings dry before arranging; fresh pineapple can be used but you’ll still need juice.
- Maraschino cherries (10): For color and a sweet accent in each ring.
- All-purpose flour (2 cups): Gives structure while keeping the cake soft.
- Baking powder (2 teaspoons): Helps the cake rise evenly.
- Salt (1 teaspoon): Balances sweetness.
- Granulated sugar (½ cup): Provides sweetness in the batter without heaviness.
- Eggs (2): Bind the batter and add richness.
- Milk (½ cup): Keeps the batter smooth and tender.
- Almond extract (1 teaspoon): Adds a warm bakery aroma; swap vanilla if preferred.
- Optional nuts: Chopped walnuts or pecans can be sprinkled in the pan for extra texture.
How to Make Pineapple Upside Down Cake
Prep. Preheat the oven to 350°F. Grease a 9×13-inch baking dish.
Sauce. Melt ½ cup butter in a medium saucepan over medium heat. Stir in 1 cup brown sugar and bring to a boil, stirring frequently. Boil 1 minute, then pour the caramel into the prepared pan.
Add fruit. Drain the pineapple, reserving ½ cup juice. Arrange the rings over the caramel to cover the bottom of the pan, trimming as needed. Place a cherry in the center of each ring. If using nuts, sprinkle them in before arranging the fruit.
Batter. In a medium bowl, whisk together 2 cups flour, 2 teaspoons baking powder, and 1 teaspoon salt. In a large bowl, beat the softened ½ cup butter with ½ cup granulated sugar and the remaining ½ cup brown sugar until combined. Add the eggs and mix well. Add the dry ingredients and beat until combined. While mixing, add ½ cup milk, ½ cup reserved pineapple juice, and 1 teaspoon almond extract. Spread the batter gently and evenly over the pineapple slices.
Bake. Bake 35–40 minutes, until a toothpick inserted in the center comes out clean. Let the cake cool at least 30 minutes so the caramel sets slightly.
Serve. Run a sharp paring knife or rubber spatula around the inner edge of the pan. Place a serving platter larger than the pan on top, hold the platter and pan firmly, and flip. Let it sit for a few minutes so the caramel releases, then carefully remove the pan. Serve warm or at room temperature, optionally with a scoop of vanilla ice cream.
Kristyn’s Recipe Tips
- Pat the pineapple. Dry the rings before arranging to keep the caramel glossy.
- Keep it neat. Spread the batter gently so the fruit pattern remains intact after flipping.
- Bake until the center springs back and a toothpick is clean, then cool at least 30 minutes.
- Invert with confidence. Loosen the edges, flip onto a platter, and let the pan rest a few minutes so the caramel releases cleanly.
- Use different pans:
- Cast iron skillet. Preheat skillet; bake at 325°F about 40–45 minutes.
- Bundt pan. Bake at 350°F for 35–40 minutes.
- Two 9-inch rounds. Bake at 375°F for 30–35 minutes.
Pineapple Upside Down Cake Recipe
Equipment
-
9×13 baking dish
Video
Ingredients
- 1 cup unsalted butter, divided
- 1½ cups packed light brown sugar, divided
- 1 (20-ounce) can pineapple rings in juice
- 10 maraschino cherries
- 2 cups all-purpose flour
- 2 teaspoons baking powder
- 1 teaspoon salt
- ½ cup granulated sugar
- 2 eggs
- ½ cup milk
- 1 teaspoon almond extract
Instructions
-
Preheat the oven to 350°F. Grease a 9×13-inch baking dish.
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Melt ½ cup butter in a medium pot over medium heat. Set remaining ½ cup butter aside to soften.
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Stir 1 cup brown sugar into the butter and bring to a boil, stirring frequently. Boil 1 minute, then pour into the prepared pan.
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Drain pineapple, reserving ½ cup juice, and arrange rings in the pan. Place a cherry in each ring. Set aside.
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Whisk flour, baking powder, and salt in a medium bowl.
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Beat softened ½ cup butter with granulated sugar and remaining ½ cup brown sugar until combined. Add eggs and mix well.
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Add the flour mixture and beat until combined.
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While mixing, add milk, ½ cup reserved pineapple juice, and almond extract.
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Spread the batter carefully over the pineapple slices.
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Bake 35–40 minutes until a toothpick comes out clean. Cool at least 30 minutes.
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Run a paring knife or spatula around the pan. Invert onto a platter larger than the pan, let rest a few minutes, then remove the pan and enjoy.
Notes
- Cast iron skillet. Preheat and bake at 325°F for about 40–45 minutes.
- Bundt pan. Bake at 350°F for 35–40 minutes.
- Two 9-inch rounds. Bake at 375°F for 30–35 minutes.
Make ahead. Make 1–2 days ahead and store covered on the counter or in the fridge. Wrap in plastic and foil to freeze for up to 2 months.
Storage. Store covered at room temperature up to 2 days, in the refrigerator about 3 days, or in the freezer up to 2 months.
Nutrition
Nutrition information is an approximation.
Recipe FAQ
Make 1–2 days ahead and store covered on the counter or in the fridge. For longer storage, wrap tightly and freeze up to 2 months.
Store covered at room temperature up to 2 days, refrigerated about 3 days, or frozen up to 2 months.
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This recipe was first posted in June, 2015.