Mini Pineapple Upside Down Cheesecakes

Category: Indulgent Desserts for Sweet Endings

Enjoy the best of both worlds with these mini pineapple upside down cheesecakes. Each bite offers a layer of buttery brown sugar pineapple and maraschino cherry atop a rich, creamy cheesecake base, all set over a delicate vanilla wafer crust. Easy to serve and great for gatherings, these personal-sized treats deliver a perfect balance of tropical fruitiness and smooth decadence. They’re simple to make ahead, chill beautifully, and reveal their fun upside down surprise when served. Bring a taste of summer to any occasion and watch them disappear as soon as they’re set out!

A woman wearing a chef's hat and apron.
Created By Sarah
Last updated on Sat, 18 Oct 2025 01:25:11 GMT
Mini pineapple upside down cheesecakes with cherries on top. Save
Mini pineapple upside down cheesecakes with cherries on top. | sarahmeal.com

Sweet tangy and wonderfully creamy these Mini Pineapple Upside Down Cheesecakes are the dessert I bring to every summer party or potluck because they get rave reviews without fail The caramelized pineapple and cherry topping is the perfect partner for a rich cheesecake layer sitting on a soft vanilla cookie crust They are bite size which means easy serving and zero fuss when it comes time for dessert

I first made these to brighten up a rainy spring brunch and now they are my go to for any special occasion My family always asks for the version with fresh pineapple because it tastes even more vibrant

Ingredients

  • Unsalted butter: melts into the brown sugar for a caramel like pineapple topping Choose high quality butter for rich flavor
  • Light brown sugar: For that classic caramel note in the topping Fresh and soft sugar melts best
  • Pineapple rings: either fresh or canned work Both give plenty of tang and a beautiful color Choose uniform pieces for even baking
  • Maraschino cherries: offer a bright sweet pop in the center They make each cheesecake extra pretty
  • Vanilla wafer crumbs: provide a soft sweet crust Use fresh cookies and pulse just before making the crust
  • Granulated sugar: keeps both crust and filling lightly sweet Go for fine sugar so it blends easily
  • Cream cheese: the heart of the filling Choose block style cream cheese that is full fat and softened for best results
  • Eggs: bind and add richness to the filling Select large eggs at room temperature for a smoother batter
  • Vanilla extract: brings warmth and enhances every layer Use pure extract if possible for best flavor
  • Sour cream: a small addition that makes the filling super creamy and slightly tangy
  • Pinch of salt: brightens all the flavors and balances the sweetness

Step-by-Step Instructions

Prepare the Muffin Pan:
Preheat your oven to three hundred twenty five degrees Fahrenheit Place cupcake liners in your muffin tray or grease it well so the cheesecakes pop out easily later
Make the Pineapple Topping:
Melt butter then whisk with brown sugar Spoon a little of this into each cup Layer two pineapple wedges in a fan Lastly press a cherry gently in the center if you like a classic look
Make the Crust:
Mix vanilla wafer crumbs with sugar and melted butter until the texture is like damp sand Spoon it evenly into each muffin cup over the pineapple Then use the back of a spoon or a small glass to press gently and make a smooth base
Make the Cheesecake Filling:
Beat cream cheese until perfectly smooth Add sugar and mix well Crack in eggs one at a time blending after each Stir in vanilla sour cream and a pinch of salt for a creamy glossy batter
Fill and Bake:
Add spoonfuls of cheesecake mixture over each crust filling almost to the top Smooth the tops gently Bake for about twenty to twenty two minutes The cakes should look set with a slight jiggle in the center
Cool and Chill:
Let cheesecakes rest in the pan for ten minutes so they firm slightly Transfer to a wire rack and cool more Then refrigerate for three hours until firm and well chilled
Unmold and Serve:
Carefully remove the cheesecakes from liners or loosen gently with a thin knife Invert onto a plate so the pineapple and cherry are on top Serve either cold for a firmer bite or let stand at room temperature for extra creaminess
Mini pineapple upside down cheesecakes with cherries on top. Save
Mini pineapple upside down cheesecakes with cherries on top. | sarahmeal.com

The pineapple is my favorite part especially when the edges caramelize in the muffin pan My nieces love helping place the cherries and always compete for the piece with the prettiest fruit on top We make these together for birthdays and the smell always reminds me of family time in the kitchen

Storage Tips

Keep your finished cheesecakes chilled in a tight container up to five days For longer storage wrap each cheesecake and freeze up to two months Let them thaw overnight in the fridge Any extra topping or syrup from the pan can be spooned on just before serving for extra moisture and taste

Ingredient Substitutions

Swap vanilla wafers for graham crackers or digestive biscuits for a more caramel taste Use fresh mango or even peaches instead of pineapple for a different twist For a dairy free option dairy free cream cheese and a plant based butter can give a similar creamy texture

Serving Suggestions

Add a dollop of whipped cream and sprinkle with toasted coconut to accent the tropical flavors Arrange mini cheesecakes on a platter with fresh mango chunks strawberries and kiwi for a colorful dessert tray These are just the right light treat following barbecue or spicy grilled meals

Mini pineapple upside down cheesecakes. Save
Mini pineapple upside down cheesecakes. | sarahmeal.com

Cultural Context

Pineapple upside down cake has long been a classic in American baking Emerging in the early twentieth century when pineapple became widely available in cans the cake’s upside down format showcased fruit and caramel in a charming presentation Blending this concept with creamy cheesecake turns a vintage favorite into a modern eye catching dessert

Common Recipe Questions

→ Can I substitute other fruits for pineapple?

Absolutely! Mango, peach, or even berries make excellent alternatives for the fruit topping, adding different flavors and colors.

→ What can I use instead of vanilla wafers for the crust?

You can use graham crackers or digestive biscuits. Both work well and provide a tasty, crumbly base for the dessert.

→ Is it possible to make these without cupcake liners?

Yes. Just ensure you generously grease the muffin pan and gently unmold the cheesecakes after they’ve chilled completely.

→ How do I make this gluten-free?

Choose gluten-free cookies for the base. This simple switch will ensure your dessert is safe for those avoiding gluten.

→ Can these be made ahead of time?

These mini cheesecakes are easily prepared in advance. Chill them for several hours or overnight for best results.

Mini Pineapple Upside Down Cheesecakes

Individual cheesecakes with brown sugar pineapple topping over creamy filling and vanilla cookie crust.

Preparation Time
20 minutes
Cook Time
22 minutes
Total Duration
42 minutes
Created By: Sarah

Recipe Category: Desserts

Level of Difficulty: Moderate

Cuisine Style: American

Servings Yield: 12 Portion Size (12 mini cheesecakes)

Diet Preferences: Vegetarian-Friendly

What You'll Need

→ Pineapple Topping

Ingredient 01 60 g unsalted butter, melted
Ingredient 02 65 g light brown sugar, packed
Ingredient 03 6 pineapple rings (fresh or canned), cut into quarters
Ingredient 04 6 maraschino cherries (optional, for decoration)

→ Crust

Ingredient 05 90 g vanilla wafer crumbs (approximately 20 wafers)
Ingredient 06 25 g granulated sugar
Ingredient 07 45 g unsalted butter, melted

→ Cheesecake Filling

Ingredient 08 450 g cream cheese, softened
Ingredient 09 100 g granulated sugar
Ingredient 10 2 large eggs
Ingredient 11 5 ml vanilla extract
Ingredient 12 30 g sour cream
Ingredient 13 Pinch of salt

How to Make It

Instruction 01

Preheat oven to 160°C. Line a 12-cup muffin pan with paper liners or grease well with nonstick baking spray.

Instruction 02

Combine melted butter and brown sugar in a small bowl. Spoon 1 teaspoon of the mixture into the bottom of each muffin cavity. Arrange two pineapple pieces in each cup to form a fan, then place a maraschino cherry in the centre if desired.

Instruction 03

In a mixing bowl, blend vanilla wafer crumbs, granulated sugar, and melted butter until evenly moistened. Spoon 1 tablespoon of the crumb mixture over the pineapple layer in each cup and press gently to form a compact base.

Instruction 04

Place the cream cheese in a large bowl and beat until smooth and fluffy. Add granulated sugar and mix until incorporated. Beat in eggs one at a time, mixing well after each addition. Stir in vanilla extract, sour cream, and a pinch of salt until creamy.

Instruction 05

Spoon or scoop the cheesecake filling onto the prepared crusts, filling nearly to the top. Smooth surfaces if needed. Bake for 20–22 minutes or until centres are set but still slightly jiggly.

Instruction 06

Let cheesecakes cool in the pan for 10 minutes. Transfer to a wire rack and cool completely, then refrigerate for at least 3 hours or until firm.

Instruction 07

Carefully remove paper liners or run a knife around the edges to loosen. Invert each cheesecake onto a plate so the pineapple topping is on top. Serve chilled or at room temperature.

Additional Tips

  1. Allow cream cheese to come to room temperature for a perfectly smooth filling.
  2. For a gluten-free version, substitute gluten-free cookies for the crust.
  3. Avoid overbaking; the centre should retain a gentle jiggle for optimal texture.

Essential Tools

  • 12-cup muffin pan
  • Cupcake liners or nonstick baking spray
  • Mixing bowls
  • Electric mixer or hand whisk
  • Wire cooling rack
  • Spoon or cookie scoop
  • Offset spatula or knife

Allergy Details

Always review ingredient labels for allergens, and consult a professional if you're unsure.
  • Contains dairy (cream cheese, butter, sour cream).
  • Contains eggs.
  • Contains gluten (wafer cookies); use gluten-free cookies if needed.

Nutritional Breakdown (per serving)

These nutritional details are for informational purposes and shouldn't replace medical advice.
  • Calories: 290
  • Fat Content: 19 grams
  • Carbohydrate Content: 26 grams
  • Protein Content: 4 grams