The Best Pineapple Upside-Down Cake Recipe 
A beautifully caramelized, gooey, and tender classic cake that’s perfect for any occasion.
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For the Topping:
1/2 cup unsalted butter (1 stick)
1 and 1/3 cups packed brown sugar
3 and 1/2 cups fresh pineapple chunks (or canned pineapple rings)
For the Cake Batter:
2 and 2/3 cups all-purpose flour
2 cups granulated sugar
1 tablespoon baking powder
1 teaspoon salt
2/3 cup vegetable oil
1 and 1/2 cups milk + 1 tablespoon white vinegar (to make buttermilk)
2 large eggs, lightly beaten
1 teaspoon pure vanilla extract
Instructions:
1. Preheat the Oven:
Set your oven to 350°F (175°C).
Place 1/2 cup of butter in a 9×13-inch glass baking pan and place it in the oven until melted.
2. Make the Caramelized Topping:
Once the butter is melted, remove the pan from the oven.
Sprinkle the brown sugar evenly over the melted butter.
Arrange the pineapple chunks in a single layer on top of the brown sugar.
Set the pan aside.
3. Prepare the Cake Batter:
In a large bowl, whisk together the flour, sugar, baking powder, and salt.
Add the vegetable oil, buttermilk (milk + vinegar), eggs, and vanilla extract to the dry ingredients.
Mix on low for 30 seconds just to combine.
Increase the mixer speed to high and beat for 3 minutes, scraping the sides of the bowl occasionally.
4. Assemble the Cake:
Carefully pour the cake batter over the pineapple and brown sugar layer in the pan.
Place the cake pan on a jelly roll pan or line the oven rack with aluminum foil to catch any potential drips.
5. Bake:
Bake for 55-65 minutes, or until a toothpick inserted into the center comes out with a few moist crumbs.
6. Flip and Serve:
Remove the cake from the oven.
Run a butter knife around the edges to loosen the cake.
Immediately place a large platter or clean jelly roll pan over the baking dish.
Carefully flip the cake over, allowing it to rest for about 3 minutes before removing the baking pan.
Let the caramelized brown sugar drizzle over the cake.
7. Serve:
Slice and serve your delicious Pineapple Upside-Down Cake warm, at room temperature, or chilled.
Optionally, top with sweetened whipped cream and maraschino cherries.
Pro Tips:
Make sure to flip the cake while it’s still warm to avoid sticking.
For a prettier presentation, use pineapple rings and place a maraschino cherry in the center of each ring.
You can also add a touch of cinnamon or nutmeg to the batter for a spiced version.
Nutritional Information (Per Slice):
Calories: ~300 kcal
Protein: 4g
Fat: 12g
Carbohydrates: 45g