Name: Pineapple Upside Down Cake Recipe
Prep time: 20 min
Cook time: 35 min
Total time: 1 h 55 min
Cuisine: American
Ingredients: 1/2 cup unsalted butter; 3/4 cup brown sugar; 18 oz can pineapple rings in pineapple juice, drained (about 12 slices); 10-14 maraschino cherries (about 12 for decoration); 2 cups all-purpose flour; 2 tsp baking powder; 1/4 tsp salt; 1/2 cup unsalted butter, softened to room temperature; 1/2 cup granulated sugar; 1/4 cup dark brown sugar; 2 large eggs; 1/2 cup whole milk; 1/2 cup pineapple juice (reserved from canned pineapple); 1 tsp vanilla extract

Jump to Recipe

If you’ve never tried a Pineapple Upside Down Cake, get ready to fall in love with a classic dessert that’s bursting with tropical sweetness and buttery caramel goodness. This show-stopping cake flips tradition on its head by layering juicy pineapple rings and bright maraschino cherries beneath a golden, tender cake, creating a stunning presentation once inverted. Every bite offers a perfect harmony of moist cake and sticky, caramelized fruit that feels both nostalgic and delightfully fresh. Whether it’s a family gathering or just a special treat at home, this Pineapple Upside Down Cake will bring joy and smiles to the table.

Pineapple Upside Down Cake Recipe - Recipe Image

Ingredients You’ll Need

The magic of this Pineapple Upside Down Cake lies in its simple yet purposeful ingredients, each playing a key role in building flavor, texture, and that irresistible caramelized top. From creamy butter for richness to the tangy pineapple juice for added moisture, these staples come together effortlessly to create a moist and flavorful cake that’s pure comfort in every bite.

Butter (1/2 cup plus 1/2 cup softened): Provides rich flavor and tender crumb to the cake and caramel base.
Brown sugar (3/4 cup and 1/4 cup dark): Essential for the caramel sauce and adds deep, molasses notes.
Pineapple rings (18 oz can, drained): Juicy, sweet fruit that forms the cake’s delicious, decorative topping.
Maraschino cherries (10-14): Adds pops of color and cheerful sweetness nestled inside pineapple slices.
All-purpose flour (2 cups): The cake’s base, providing structure and softness.
Baking powder (2 tsp): Helps the cake rise light and fluffy.
Salt (1/4 tsp): Enhances all other flavors for balanced taste.
Granulated sugar (1/2 cup): Sweetens the cake without weighing it down.
Eggs (2 large): Bind ingredients and add richness to the batter.
Whole milk (1/2 cup): Keeps the cake moist and tender.
Pineapple juice (1/2 cup, reserved): Adds a subtle tropical zing and keeps the batter perfectly moist.
Vanilla extract (1 tsp): Brings warmth and aromatic depth to the cake’s flavor.

How to Make Pineapple Upside Down Cake

Step 1: Prepare the Caramel Base

Start by melting 1/2 cup of butter and 3/4 cup brown sugar together in a saucepan over medium heat. Stir constantly until the butter fully melts and the sugar dissolves, transforming into a sticky, amber caramel sauce. This luscious base is what creates the signature sweet and glossy topping of your cake, so take your time to get it just right.

Step 2: Arrange the Pineapple and Cherries

Preheat your oven to 350°F and lightly grease a 9×13 baking dish. Pour the warm caramel sauce evenly into the dish, spreading it out with a spatula. Next, arrange the pineapple rings in neat rows, starting with a row in the center and working outward to create a balanced pattern. Pop one maraschino cherry into the center of each pineapple ring, and feel free to add extra cherries in any open spaces for that festive look.

Step 3: Mix Dry Ingredients

In a medium bowl, whisk together the 2 cups of all-purpose flour, 2 teaspoons of baking powder, and 1/4 teaspoon salt. Combining these dry ingredients ensures your cake will rise evenly and develop a perfect crumb texture.

Step 4: Cream the Sugars and Butter

In a larger bowl, beat 1/2 cup softened butter with 1/2 cup granulated sugar and 1/4 cup dark brown sugar using a hand mixer until the mixture is light, fluffy, and creamy. This step is crucial for incorporating air that helps the cake stay tender and moist.

Step 5: Add Eggs

Add the eggs one at a time to the creamed butter and sugars, mixing well after each addition. The eggs bind everything together, contributing to the cake’s lush texture.

Step 6: Combine the Batter

Gradually add the dry ingredients to the wet mixture and mix just until combined. Then pour in the whole milk, pineapple juice, and vanilla extract. Stir gently until your batter is smooth and velvety, perfectly ready to be spread over your pineapple and caramel base.

Step 7: Bake the Cake

Spoon the batter evenly over the pineapple rings and smooth it out with a spatula. Place the baking dish in the oven and bake for 30 to 35 minutes until the edges turn golden and a toothpick inserted in the center comes out clean. This means your cake is perfectly cooked and ready for its big reveal.

Step 8: Cool and Invert

Allow the cake to cool in the pan for at least an hour so the caramel sets nicely. When you’re ready, cover the pan with a large baking sheet or cutting board, hold them firmly, and flip the cake over. The pineapple and cherry topping will now be gloriously displayed on top, making it almost too pretty to eat!

How to Serve Pineapple Upside Down Cake

Garnishes

A light dusting of powdered sugar or a dollop of freshly whipped cream makes a simple, elegant garnish that doesn’t overpower the cake’s rich flavors. For an extra tropical twist, serve with toasted coconut flakes or a sprinkle of chopped nuts for a delightful crunch.

Side Dishes

This Pineapple Upside Down Cake pairs beautifully with a scoop of vanilla ice cream or a refreshing tropical fruit salad. The creamy cold ice cream complements the warm, sticky cake perfectly, while fresh fruits keep the meal feeling light and balanced.

Creative Ways to Present

For gatherings, serve individual slices topped with a maraschino cherry and a sprig of fresh mint to brighten the plate. You could also use mini versions of the cake baked in muffin tins for charming single servings that invite guests to dig in with their eyes first.

Make Ahead and Storage

Storing Leftovers

Once cooled, store leftover Pineapple Upside Down Cake covered with plastic wrap or in an airtight container at room temperature for up to two days. If your kitchen tends to be warm, the fridge is a good option to keep the caramel topping from becoming too soft.

Freezing

You can freeze leftover cake by wrapping it tightly in plastic and then in aluminum foil to prevent freezer burn. It will keep well for up to two months. Thaw it overnight in the fridge before serving to maintain its best texture and flavor.

Reheating

Reheat slices gently in the microwave for about 20 seconds or warm a slice in a 300°F oven for 10-15 minutes to bring back that freshly baked warmth and soft texture. Just be careful not to overheat, so the cake doesn’t dry out.

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple can add a vibrant flavor, but be sure to slice it evenly and pat it dry to avoid excess moisture that could affect the caramel topping.

What if I don’t have maraschino cherries?

No worries! You can omit them or substitute with other colorful fruit like halved raspberries or small slices of strawberry for a fresh twist.

How do I know when the cake is done?

Check doneness by inserting a toothpick into the center of the cake. If it comes out clean or with a few moist crumbs, the cake is perfectly baked and ready to cool.

Can I make this cake gluten-free?

Yes, substitute the all-purpose flour with a gluten-free blend made for baking. Make sure it contains xanthan gum for the best texture.

Is it possible to make this cake vegan?

You can try swapping the butter for vegan margarine and using flax eggs or other egg substitutes. Keep in mind the texture and flavor might vary slightly but it will still be delicious.

Final Thoughts

Making and sharing a Pineapple Upside Down Cake is like giving a warm hug through dessert — it’s comforting, sweet, and a little bit fancy all at once. This classic recipe is simple enough for any home cook to master but special enough to impress family and friends. So preheat your oven, gather these lovely ingredients, and enjoy crafting a cake that’s as joyful to make as it is to eat. Trust me, once you try it, Pineapple Upside Down Cake will become your go-to recipe whenever you want to add a touch of sunshine to your day.

Pineapple Upside Down Cake Recipe

★★★★★

4.8 from 28 reviews

Author: Sophie
Total Time: 1 hour 55 minutes
Yield: 12 servings 1x
Diet: Vegetarian

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Description

A classic Pineapple Upside Down Cake made with caramelized brown sugar, juicy pineapple rings, and maraschino cherries. This moist and flavorful cake features a buttery topping caramelized to perfection and a tender vanilla-infused batter, perfect for any occasion.

Instructions

Prepare the caramel topping: Heat 1/2 cup unsalted butter and 3/4 cup brown sugar in a saucepan over medium heat, stirring constantly until the butter melts and the sugar dissolves into a smooth caramel sauce.
Preheat oven and prepare pan: Preheat the oven to 350°F (175°C). Lightly grease a 9×13 inch baking dish with nonstick cooking spray. Pour the warm caramel sauce evenly into the bottom of the baking dish and spread it with a spatula.
Arrange pineapple and cherries: Place pineapple rings neatly in rows, starting with the middle row then filling around it. Place one maraschino cherry in the center of each pineapple ring and add extra cherries in gaps between the slices as desired.
Mix dry ingredients: In a medium bowl, whisk together 2 cups all-purpose flour, 2 tsp baking powder, and 1/4 tsp salt until evenly combined.
Cream butter and sugars: In a large bowl, use a hand mixer to cream 1/2 cup softened unsalted butter, 1/2 cup granulated sugar, and 1/4 cup dark brown sugar until fluffy and creamy.
Add eggs: Beat in the eggs one at a time, mixing well after each addition until smooth and fully incorporated.
Combine dry and wet ingredients: Gradually add the dry ingredients to the creamed butter mixture, mixing just until combined to avoid overmixing.
Add liquids: Pour in 1/2 cup whole milk, 1/2 cup reserved pineapple juice, and 1 tsp vanilla extract. Mix gently until all ingredients form a smooth cake batter.
Assemble and bake: Carefully spread the cake batter evenly over the pineapple and cherry layer in the baking dish using a spatula. Bake in the preheated oven for 30-35 minutes or until the edges turn golden brown and a toothpick inserted in the center comes out clean.
Cool and invert: Allow the cake to cool in the pan for at least 1 hour. To serve, place a baking sheet or large cutting board over the pan, hold them firmly together, and carefully flip the pan to invert the cake onto the board with the pineapple layer on top. Slice around the pineapple rings and serve.

Notes

Make sure to cool the cake completely before flipping to prevent the topping from sticking or breaking.
You can substitute fresh pineapple slices if preferred, but canned pineapple provides consistent sweetness and moisture.
Using dark brown sugar in the batter adds a richer molasses flavor to complement the caramel topping.
To avoid sticking, ensure the pan is well-greased or use parchment paper underneath caramel if desired.
Leftover cake can be stored covered at room temperature for up to 2 days or refrigerated for up to 4 days.

Prep Time: 20 minutes
Cook Time: 35 minutes
Category: Dessert
Method: Baking
Cuisine: American