Mini Pineapple Upside-Down Cheesecakes Recipe

My mother’s kitchen always smelled of caramelized pineapple and warm vanilla when I was growing up.

I created my Mini Pineapple Upside-Down Cheesecakes as a tribute to those sweet memories of standing on a step stool, watching her transform humble ingredients into something magical.

I still feel that childhood excitement every time I flip each little dessert to reveal its glistening golden top – pure kitchen magic that captivates me to this day.

I’ve perfected the balance of tangy cream cheese with sweet, caramelized pineapple in every bite-sized treasure.

Why These Mini Pineapple Upside-Down Cheesecakes Are a Must-Try

The beauty of these mini cheesecakes is how they combine two beloved desserts into something even more spectacular than the sum of their parts.

I adore how the buttery brown sugar topping caramelizes around the pineapple, creating that signature sticky-sweet flavor that contrasts perfectly with the tangy cheesecake base.

They’re perfect for gatherings since they’re already portioned out—no messy cutting or serving required!

Plus, they look absolutely stunning on a dessert table with their golden pineapple tops and bright cherry centers.

This Mini Pineapple Upside-Down Cheesecakes recipe always brings a smile to my face—just like my Easy Strawberry Lemon Blondies and Creamy Strawberry Cheesecake Cookies. You’ve got to try them next!

Ingredients for Mini Pineapple Upside-Down Cheesecakes

For the Pineapple Topping:

• 4 tablespoons unsalted butter, melted
• ⅔ cup brown sugar, packed
• 1 can (20 oz) pineapple rings, drained (reserve juice!)
• 12 maraschino cherries, patted dry

For the Graham Cracker Base:

• ¾ cup graham cracker crumbs
• 2 tablespoons granulated sugar
• 3 tablespoons unsalted butter, melted

For the Cheesecake Filling:

• 16 oz cream cheese, softened at room temperature
• ½ cup light brown sugar
• 2 tablespoons all-purpose flour
• ⅓ cup sour cream, room temperature
• ¼ cup reserved pineapple juice
• 1 teaspoon pure vanilla extract
• 2 large eggs, room temperature

My secret tip: Don’t substitute low-fat cream cheese here—the full-fat version gives these mini cheesecakes their heavenly texture and helps them set properly.

How to Make Mini Pineapple Upside-Down Cheesecakes

Step 1: Prepare Your Pans

Preheat your oven to 325°F. Line a standard 12-cup muffin tin with cupcake liners. I recommend using sturdy foil liners for easier removal later.

Step 2: Create the Pineapple Layer

In a small bowl, mix the melted butter and brown sugar until well combined. Divide this mixture evenly among the muffin cups (about 1 tablespoon per cup).

Cut pineapple rings into quarters. Place two quarter-pieces into each muffin cup, arranging them on top of the brown sugar mixture. Add a maraschino cherry in the center of each cup.

Step 3: Make the Graham Cracker Base

Mix graham cracker crumbs, sugar, and melted butter until the mixture resembles wet sand. Spoon about 1 tablespoon over the pineapple in each cup and gently press down.

Step 4: Prepare the Cheesecake Filling

In a large bowl, beat cream cheese on low speed until smooth. Add brown sugar and flour, continuing to mix on low until well combined and no lumps remain.

Mix in sour cream, pineapple juice, and vanilla extract. Add eggs one at a time, mixing on low speed just until incorporated after each addition. Over-mixing will add too much air to the batter, which can cause cracks.

Step 5: Assemble and Bake

Divide the cheesecake batter evenly among the muffin cups, filling each about ¾ full.

Place the muffin tin in a larger baking pan. Pour hot water into the larger pan until it reaches about halfway up the sides of the muffin tin. This water bath helps the cheesecakes bake evenly.

Bake for 20-25 minutes, until the edges are set but centers still have a slight jiggle.

Step 6: Cool and Flip

Turn off the oven and crack the door open. Let the cheesecakes cool in the oven for 30 minutes, then remove and cool completely at room temperature.

Refrigerate for at least 4 hours or overnight. When ready to serve, carefully remove the liners and invert each cheesecake onto a serving plate so the pineapple layer is on top.

Can I use fresh pineapple instead of canned?

While fresh pineapple has amazing flavor, I don’t recommend it for this recipe. Canned pineapple has consistent sweetness and moisture content that works perfectly here.

Fresh pineapple contains enzymes that can prevent the cheesecake from setting properly.

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Pro Tips for Perfect Mini Pineapple Upside-Down Cheesecakes

The number one mistake I made when first creating these was rushing the cooling process. Patience truly pays off!

Allow them to cool gradually in the oven with the door cracked, then at room temperature, before finally chilling in the fridge.

This gentle transition prevents those frustrating cracks and ensures a perfectly smooth texture.

For the smoothest cheesecake filling, make sure all refrigerated ingredients are truly at room temperature before mixing.

I take mine out at least an hour beforehand. And remember to tap your muffin tin gently against the counter after filling to release any trapped air bubbles.

Can I make these Mini Pineapple Upside-Down Cheesecakes ahead of time?

Absolutely! These actually taste better the next day after the flavors have had time to meld.

You can make them up to 3 days in advance and keep them refrigerated until ready to serve. Just wait to flip them onto serving plates until shortly before serving.

Can I freeze these mini cheesecakes?

Yes, these freeze beautifully! After they’ve fully chilled, wrap each one individually in plastic wrap and then foil.

Freeze for up to 1 month. Thaw overnight in the refrigerator before flipping and serving.

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My cheesecakes cracked. What went wrong?

Cracking usually happens when cheesecakes cool too quickly or are overcooked. Next time, try reducing your oven temperature by 25°F and follow the gradual cooling method in the recipe.

Remember, even if they crack, they’ll still taste amazing, and the pineapple topping will hide any imperfections!

Sweet Ways to Enjoy These Tropical Mini Treats

I love serving these Mini Pineapple Upside-Down Cheesecakes on my grandmother’s vintage dessert plates for family brunches.

The bright, sunny appearance makes them perfect for spring and summer gatherings, though I’ve been known to make them year-round whenever I need a tropical escape!

They’re substantial enough to serve on their own, but for an extra-special presentation, I sometimes add a dollop of homemade whipped cream and a light sprinkle of toasted coconut flakes.

My kids enjoy them with a scoop of vanilla ice cream on the side for an over-the-top dessert experience.