A classic pineapple upside-down cake that everyone will enjoy. Sweet pineapple and cherries baked in rich brown sugar butter topping and tender vanilla cake.
There’s a wave of innovative and ultra modern desserts out there nowadays, but I found myself in the mood for some nostalgic baked treats that make people reminisce of the good ole’ days. That’s why this recipe calls for a delicious classic pineapple upside-down cake, yum! This is one of the timeless dessert creations that make me think of the days of Julia Child, white lace aprons, and dad carving the turkey.
I make this recipe because my hubby LOVES it. Jason grew up very lucky as his mom and grandma would create elegant homemade feasts. This particular dessert is a special treat that his grandma Rose whips together and he always is so happy when he gets a warm slice. I remember the first time I ever tried her version fresh from the oven, I was shocked how amazing it was. I had been missing out all of this time!
So I knew I had to ask her for the secret recipe so I could recreate this for Jason. Ladies, figuring out how to make this pineapple upside-down cake helped me seal the deal with putting a ring on it, just saying… hehe. 🙂
What makes pineapple upside down cake so addictive? I’m going to predict it’s the brown sugar and butter smear that goes down on the bottom of the pan. There’s a little bit of dark rum and vanilla bean paste that I added to the mixture for a little extra L-O-V-E, oh yeah.
When the brown butter goodness melts and cooks in the hot pan, the edges of the cake and pineapples absorb the molten caramel, and each bite becomes outrageously good.
I use a 9-inch round cake pan that is at least 2-inches deep. This allows me to add the bottom layer of pineapple rounds and two cherries in the center of each slice. I cannot believe I forgot to add the chopped walnuts! If you like nuts, Jason’s grandma adds walnuts into all of the nooks and crannies not occupied by fruit, like on the perimeter of the cake.
The walnuts get that gooey caramel coating once baked, and the crunchy sweetness is amazing. The last step is to add the cake batter on top of the pineapples and then allow to cook for about 30 to 35 minutes. Be careful not to overcook the cake as the texture can become too dry. You want the cake to spring back, yet still be very moist.
See that caramel ring on the edges and tender baked fruit that’s just snuggling with the cake? Yep, the perfect marriage of sweet, fruity and tender pieces of heaven. I’ll stop chatting and let you eat with your eyes… I’m sure by the end of this you’ll be searching through your pantry for some canned pineapples!
This beautiful pineapple upside down cake is best served warm because it smells like vanilla and caramel right out of the oven, plus the fruit is super tender. Now just grab a nice hot cup of tea or coffee and a slice of this cake, your favorite pals will appreciate you even more!
If you’re not into pineapple, this recipe is super versatile for your other favorite fruit toppings like peach, apple, strawberry, mango, really anything you’re craving. Looking for more simple and classic dessert recipes? Try some scrumptious browned butter chocolate chip pecan cookies or otherwise some white chocolate cherry cookies.
What is the benefit of using Cake Flour?
Flour is an essential ingredient in cakes because it provides structure and bulk to baked goods. Wheat flour is commonly used and contains proteins, minerals, moisture, fats, and starches. One of the key differences in cake flour versus all-purpose flour is the amount of protein. The more protein, the higher the gluten-forming potential, which contributes to volume, texture, structure and appearance. If you want a tender and soft product, it’s important to use a flour that has lower protein content, so it does not become tough when hydrated and mixed. Cake flour contains between 6 to 8 percent protein versus all-purpose has 10 to 13. This can make a big difference in the baked cakes texture. (Source: On Baking: A Textbook of Culinary Fundamentals)
Classic Pineapple Upside-Down Cake
- 1/2 cup unsalted butter, (113g, 4 ounces) softened to room temperature
- 4 1/2 teaspoons honey, (22ml)
- 1/2 teaspoon dark rum, optional
- 1 cup dark brown sugar, (198g) packed
- 1/4 teaspoon pure vanilla extract
- 7 pieces pineapple rings, canned, 3-inches wide
- 14 maraschino cherries, drained
- 1/4 cup walnuts, (28g) chopped
- 1 1/3 cups cake flour, (157g)
- 2 teaspoons double-acting baking powder, (8g)
- 1/2 cup unsalted butter, (113g, 4 ounces) softened, 60 to 65°F (16 to 18°C)
- 1/2 cup granulated sugar, plus 2 more tablespoons (123g)
- 1/2 teaspoon pure vanilla extract, (2.5ml)
- 2 large eggs, room temperature
- 4 teaspoons whole milk, (20 ml) room temperature
- Adjust the oven rack to the middle position and preheat the oven to 350°F (177°C).
- Use a handheld mixer or stand mixer fitted with a paddle, combine the butter, honey, rum (if using), brown sugar, and vanilla over medium speed in a medium-sized bowl, 30 seconds.
- Lightly grease the bottom and sides of an 8 1⁄2 x 3-inch or 9 x 2-inch round pan with vegetable oil.
- Evenly spread the brown sugar mixture over the bottom of the pan.
- Place one of the pineapple slices in the middle and 6 around the edges on top of the brown sugar mixture.
- Add two cherries in the center of each pineapple ring.
- Add the walnuts to the edges of the pan where the brown sugar mixture is exposed and add small broken pieces in the center between the rings.
- Sift the flour and baking powder in a medium-size bowl. Whisk to combine.
- In a separate medium-size bowl, add the softened butter and granulated sugar. Using the paddle attachment, mix on low speed until just combined, 20 seconds. Increase the speed to medium and mix for 3 minutes until the mixture is light and creamy. Scrape down the sides as needed.
- Add the vanilla and mix on medium speed for 10 seconds.
- Add the eggs one at a time, on medium speed until creamy, 30 seconds. Scrape the bowl and repeat with the second egg.
- Add the milk and combine on medium speed, 15 seconds.
- On low speed add the flour mixture in 3 batches, mixing until just combined, 10 seconds each interval. Scrape the sides as needed. Pour the batter into the pan over the pineapples; it will be thick. Use a spatula to spread evenly in the pan.
- Bake until the cake is golden brown, springs back when touched and a toothpick inserted in the center comes out clean with a few crumbs attached, or center of the cake registers about 185 to 190°F (85 to 88°C), about 30 to 40 minutes. The bake time will depend on the size of your pan.
- Allow the cake to cool in the pan on a cooling rack for 45 to 60 minutes. The cake will still be slightly warm but will set as it will continue to cook in the pan. Do not cool completely in pan or the topping will stick to the bottom.
- Run a knife around the edges of the cake, invert onto a serving platter and serve warm.
- Leftover cake can be stored at room temperature in an airtight container for 1 day.