Grandma's Pineapple Upside Down Cake

Transport your taste buds to simpler times with Grandma's Pineapple Upside Down Cake, a retro dessert classic brimming with buttery, caramelized pineapple flavor. This timeless recipe features a beautiful mosaic of golden pineapple rings and vibrant maraschino cherries nestled in a rich brown sugar glaze, all crowned with a soft, moist vanilla cake infused with pineapple juice for extra tropical sweetness. Perfect for family gatherings or nostalgic moments, this cake comes together with just 20 minutes of prep time and will impress both in taste and presentation. Serve it warm for the ultimate comforting treat, and watch it steal the spotlight at your next dessert table!

Nutriscore Rating: 40/100

Prep Time:20 mins

Cook Time:40 mins

Total Time:60 mins

Servings: 8

Ingredients

• 6 tablespoons unsalted butter
• 0.75 cup brown sugar (packed)
• 7 pieces pineapple rings (canned, drained)
• 7 pieces maraschino cherries
• 1.5 cups all-purpose flour
• 2 teaspoons baking powder
• 0.25 teaspoon salt
• 1 cup granulated sugar
• 0.5 cup unsalted butter (softened)
• 1 teaspoon vanilla extract
• 2 large eggs
• 0.5 cup whole milk
• 0.25 cup pineapple juice (from canned pineapple)

Directions

Step 1

Preheat your oven to 350°F (175°C).

Step 2

Place 6 tablespoons of butter in a 9-inch round cake pan and melt it in the oven. Once melted, remove the pan and sprinkle the brown sugar evenly over the butter.

Step 3

Arrange the pineapple rings in a single layer over the brown sugar mixture in the pan. Place a maraschino cherry in the center of each pineapple ring.

Step 4

In a medium bowl, whisk together the flour, baking powder, and salt. Set aside.

Step 5

In a large mixing bowl, use a hand or stand mixer to beat the softened butter and granulated sugar until light and fluffy, about 2-3 minutes.

Step 6

Add the vanilla extract and eggs, one at a time, beating well after each addition.

Step 7

In a separate small bowl or measuring cup, combine the milk and pineapple juice.

Step 8

Gradually add the dry ingredients to the wet ingredients in three batches, alternating with the milk-pineapple juice mixture. Begin and end with the dry ingredients, mixing just until combined. Do not overmix.

Step 9

Pour the batter evenly over the pineapple and brown sugar layer in the prepared cake pan, spreading it out gently with a spatula.

Step 10

Bake in the preheated oven for 40-45 minutes, or until a toothpick inserted into the center comes out clean.

Step 11

Remove the cake from the oven and let it cool in the pan for 5 minutes. Run a knife around the edges of the pan to loosen the cake.

Step 12

Invert a serving plate or cake stand over the pan, then carefully flip the cake onto the plate. Let the pan sit inverted for 1-2 minutes before lifting it off.

Step 13

Allow the cake to cool slightly before serving. Enjoy warm or at room temperature.

Nutrition Facts

Serving size	(1288.1g)

Amount per serving	% Daily Value*
Calories	4015.1

Total Fat 183.4g	0%
Saturated Fat 108.4g	0%
Polyunsaturated Fat 0.1g
Cholesterol 831.0mg	0%
Sodium 1761.2mg	0%
Total Carbohydrate 575.9g	0%
Dietary Fiber 7.3g	0%
Total Sugars 419.4g
Protein 38.1g	0%

Vitamin D 194.0IU	0%
Calcium 455.5mg	0%
Iron 12.2mg	0%
Potassium 1105.2mg	0%

*The % Daily Value tells you how much a nutrient in a serving of food contributes to a daily diet. 2,000 calories a day is used for general nutrition advice.

Source of Calories

Fat: 40.2%

Protein: 3.7%

Carbs: 56.1%