Name: Pineapple Upside Down Cake Recipe – Retro Treat
Prep time: 20 min
Cook time: 40 min
Total time: 1 h
Yield: 8 servings
Cuisine: American
Ingredients: ¼ cup unsalted butter, melted; ½ cup packed light brown sugar; 7 pineapple rings (canned or fresh); 7 maraschino cherries; 1 ½ cups all-purpose flour; 1 cup granulated sugar; ½ cup unsalted butter, softened; 2 large eggs; ½ cup whole milk; 1 ½ teaspoons baking powder; ¼ teaspoon salt; 1 teaspoon vanilla extract

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Hey y'all! If you're on the hunt for a show-stopping, classic dessert that's as fun to make as it is to eat, this Pineapple Upside Down Cake Recipe – Retro Treat has you covered. With its golden, caramelized pineapple topping and ultra-moist vanilla cake, this old-school favorite brings back sweet memories and is perfect for parties, potlucks, or just a special family treat. So, grab your apron and let's get cooking!

Why You'll Love This Pineapple Upside Down Cake Recipe – Retro Treat

Super moist and buttery crumb with a caramelized topping.
Visually stunning, thanks to the jewel-like pineapple and cherry design.

Perfect balance of sweet, tangy, and rich flavors in every bite.
Simple ingredients and easy-to-follow steps for bakers of all levels.
Great make-ahead option for celebrations or a nostalgic weekend bake.

Ingredients for Pineapple Upside Down Cake Recipe – Retro Treat

½ cup (115g) unsalted butter, melted (plus extra for greasing)
¾ cup (150g) light brown sugar, packed
8-10 pineapple rings (from one 20oz can, reserve juice)

10-12 maraschino cherries, drained
1 and ½ cups (190g) all-purpose flour
1 teaspoon baking powder

½ teaspoon baking soda
¼ teaspoon salt
½ cup (115g) unsalted butter, room temperature

1 cup (200g) granulated sugar
2 large eggs, room temperature
1 teaspoon pure vanilla extract

½ cup (120ml) sour cream or plain Greek yogurt
¼ cup (60ml) pineapple juice (from can)
¼ cup (60ml) whole milk

How to Make Pineapple Upside Down Cake Recipe – Retro Treat

Step 1: Prepare the Pan & Topping

Preheat your oven to 350°F (175°C). Grease a 9-inch (23cm) round cake pan with butter.
Pour the melted butter into the bottom of the pan, spreading evenly.
Sprinkle brown sugar on top of the butter, covering the entire base.

Arrange pineapple rings over the brown sugar, fitting as many as possible without overlapping. Place a cherry in the center of each ring and fill any gaps with extra cherries.

Step 2: Mix the Cake Batter

In a bowl, whisk together flour, baking powder, baking soda, and salt.
In a large bowl, beat softened butter and sugar together until light and fluffy (about 2-3 minutes).

Add eggs one at a time, mixing well after each. Stir in vanilla extract.
Add sour cream and mix until incorporated.
Mix in the dry ingredients in three additions, alternating with the pineapple juice and milk. Start and end with the dry ingredients. Do not overmix.

Step 3: Assemble & Bake

Carefully spread the cake batter over the pineapple layer, smoothing the top.
Bake for 40-45 minutes or until a toothpick inserted in the center comes out clean.
Cool in the pan on a wire rack for 15 minutes. Run a knife around the edge, then invert the cake onto a serving plate. Let cool at least 10 more minutes before slicing.

Notes for Success with Pineapple Upside Down Cake Recipe – Retro Treat

For extra flavor, try adding a dash of cinnamon or a splash of rum to the batter.
Use the right pan size to prevent overflow and ensure even baking.
If using fresh pineapple, check out this guide on prepping pineapple.

Variations on the Classic Pineapple Upside Down Cake Recipe – Retro Treat

Spiced Version: Add ½ teaspoon ground cinnamon and ¼ teaspoon ground ginger to the dry ingredients.
Mini Cakes: Bake in muffin tins for cute, individual servings—reduce baking time to 20-25 minutes.
Vegan Option: Substitute eggs with flax eggs, dairy butter with vegan butter, and sour cream with coconut yogurt.

Required Equipment for Pineapple Upside Down Cake Recipe – Retro Treat

9-inch round cake pan (not springform)
Mixing bowls
Hand or stand mixer

Measuring cups and spoons
Rubber spatula
Wire rack

Storage Instructions: Pineapple Upside Down Cake Recipe – Retro Treat

Store leftovers tightly covered at room temperature for up to 2 days or in the refrigerator for up to 5 days. For longer storage, wrap slices tightly and freeze for up to 2 months. Thaw overnight in the fridge before serving for best taste and texture.

Suggested Pairings & Serving Recommendations

Serve warm with a scoop of vanilla ice cream or fresh whipped cream.
Pair with a cup of robust coffee or tropical fruit tea.

For brunch, enjoy a small slice with a mimosa for a festive touch!

Pro Tips for the Best Pineapple Upside Down Cake Recipe – Retro Treat

Pat the pineapple and cherries dry before arranging in the pan to prevent excess moisture.
Invert the cake while it’s still warm for a flawless release and a glossy topping.

For even more baking science, check out this cake guide from Serious Eats.

FAQ: Pineapple Upside Down Cake Recipe – Retro Treat

Can I use fresh pineapple instead of canned?: Absolutely! Just slice it into ½-inch rings and remove the core before using.
Why did my cake stick to the pan?: Make sure to generously grease the pan and invert while still warm. Any sticking may be from not enough butter or cooling too long.
Can I make this cake ahead of time?: Yes! It tastes great the next day—just store tightly wrapped in the fridge and bring to room temperature or gently reheat before serving.

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Pineapple Upside Down Cake Recipe – Retro Treat