Pineapple Upside-Down Cheesecakes

Pineapple Upside Down Cake

Oh, pineapple upside-down cake—a true classic! This dessert is the perfect balance of caramelized pineapple goodness with a soft, buttery cake. Plus, it’s got that retro vibe that makes you feel like you’re channeling some serious 1950s kitchen goddess energy. Let’s dive in and make this cake that’s as fun to look at as it is to eat.

Why You’ll Love This Recipe

First of all, it’s got fruit, so technically, you’re being healthy, right? But seriously, the combination of the juicy pineapple and sweet cherries swimming in buttery, brown sugar goodness, paired with a moist vanilla cake? It’s a flavor bomb. Plus, this cake looks so fancy when you flip it over, but it’s really just the culinary equivalent of wearing sweatpants—super comfy and easy to pull off.

Expert Tips and Tricks

Use pineapple juice from the can for extra flavor in the cake. No need to crack open a fresh pineapple when you’ve already got the goods in the pantry.

Don’t overmix. Gently stir until just combined to keep the cake light and fluffy.

When you flip the cake, be patient. Let it cool for 10 minutes before flipping, or you’ll end up with a sticky mess (trust me, I’ve been there).

Foil is your friend. Tent the cake after 20 minutes of baking to keep it golden instead of… well, burnt.

Pineapple Upside-Down Cheesecakes
Pineapple Upside-Down Cheesecakes
Pineapple Upside-Down Cheesecakes

Recipe Variations and Possible Substitutions

Don’t have maraschino cherries? No problem! You can swap them out for fresh cherries, raspberries, or even blueberries. The color pop is still there, and they bring a fresh flavor.

Gluten-free? Sub out the all-purpose flour for a 1:1 gluten-free flour blend, and you’re good to go.

Want to make it boozy? Add a splash of rum to the topping for a tropical twist—piña colada vibes in cake form!

Serving and Pairing Suggestions

Serve this cake warm with a scoop of vanilla ice cream or a dollop of whipped cream. The cold creaminess against the warm, sticky cake is a match made in heaven. If you want to go over the top (and why wouldn’t you?), drizzle a little caramel sauce over the whole thing. I mean, live your best life!

Storage and Reheating Tips

Got leftovers (like that’s a thing)? Cover the cake tightly and keep it in the fridge for up to 3 days. To reheat, pop a slice in the microwave for about 15-20 seconds. It’ll be just as moist and gooey as when it came out of the oven.

Can I use fresh pineapple instead of canned?

Absolutely! Just make sure you slice it thin enough to cook through properly. But honestly, canned pineapple is perfect for this recipe because it’s already the right texture and sweetness.

What if my cake sticks to the pan when I flip it?

Make sure you greased your pan well before adding the butter and brown sugar. If it still sticks, run a butter knife around the edges of the pan and try to flip again. Worst case, you’ve got a delicious mess on your hands.

How do I store the cake if I don’t have a cheesecake to put it on top of?

Haha, no worries! You can store the cake just like any other—either in an airtight container or tightly wrapped in plastic wrap. The cheesecake part was just an extra fancy suggestion.

Pineapple Upside-Down Cheesecakes

Pineapple Upside-Down Cake Recipe

Prep Time 15 minutes
Cook Time 45 minutes
Total Time 1 hour
Course Dessert
Calories 350 kcal

Ingredients
  

  • 1 and 2/3 cups flour
  • ½ teaspoon baking powder
  • ¼ teaspoon baking soda
  • ½ teaspoon salt
  • ½ cup butter melted
  • ¾ cup packed light brown sugar
  • ¼ cup granulated sugar
  • 1 large egg
  • ¾ cup milk
  • ¼ cup pineapple juice from the canned pineapples
  • 1 teaspoon vanilla extract

Instructions
 

  • Preheat your oven to 350°F (175°C).
  • Topping: Pour the melted butter into a 9-inch cake pan, then sprinkle the brown sugar evenly on top. Arrange the pineapple slices over the sugar, placing cherries in the center of each pineapple ring.
  • Cake Batter: In a microwave-safe bowl, melt the butter. Whisk in the brown sugar and granulated sugar until smooth. Add the egg, milk, pineapple juice, and vanilla extract, whisking until combined.
  • In a separate bowl, whisk together the flour, baking powder, baking soda, and salt. Add the dry ingredients to the wet ingredients and stir just until combined. Don’t overmix!
  • Pour the batter over the pineapples and cherries in the cake pan.
  • Bake for 20 minutes, then tent the cake loosely with foil to prevent excessive browning. Bake for an additional 20-25 minutes, or until a toothpick inserted into the center comes out clean.
  • Let the cake cool for 10 minutes before inverting it onto a large plate. Allow it to cool completely before slicing and serving.

Notes

  • Pineapple Juice Tip: Don’t toss the juice from the canned pineapples! Use it in the cake batter to amp up that tropical flavor.
  • Foil Trick: Tent your cake with foil after 20 minutes of baking to prevent it from turning into a golden brown hockey puck. You want golden, not charred.
  • Flipping Nerves? Don’t panic when it’s time to invert the cake. Let it cool for those 10 minutes so it slides out easier. And if a pineapple slice gets stuck? Just plop it back on top like nothing happened.
  • Make Ahead: You can bake this cake the night before, but good luck not eating it in the middle of the night!
  • Calories: Roughly 350 per slice (but who’s counting when it’s this good?)
Keyword Dessert Recipe