Pineapple Upside-Down Cheesecake

Section: Classic American Desserts: Timeless Treats for Every Sweet Tooth

Discover a decadent blend of juicy pineapple and maraschino cherries nestled beneath a luscious, silky cheesecake filling. This treat features a buttery graham cracker crust and is finished upside-down for a stunning presentation. The method ensures a creamy texture with vibrant fruit flavors in every slice. Setting the pan in a water bath yields a perfectly smooth and rich result, making this dessert ideal for special occasions or any time you crave something out of the ordinary.

iamcooker.com
Sofia Pitt sofia
Most recent update: Mon, 01 Dec 2025 15:29:31 GMT
A slice of pineapple upside-down cheesecake. Save
A slice of pineapple upside-down cheesecake. | iamcooker.com

This Pineapple Upside-Down Cheesecake is my favorite way to bring a splash of sunshine to any table. Sweet pineapple and cherries meet ultra-creamy cheesecake for a stunning dessert that dazzles every time. Upside-down cakes are fun, but adding a thick cheesecake layer transforms this classic into something unforgettable.

The first time I made this, my family could not believe it was homemade. Now it is always requested for birthdays and summer BBQs.

Ingredients

  • Graham cracker crumbs: Give the base the perfect crunch while holding up under a juicy topping. Choose plain honey grahams for best results.
  • Unsalted butter: Holds the crust together and provides a rich taste. Opt for fresh butter with no off-smell.
  • Brown sugar: Creates a caramelized layer under the fruit. Look for soft, moist light brown sugar for even melting.
  • Pineapple rings: Deliver the bright tropical flavor and striking pattern. Use firm canned rings or ripe but not overripe fresh fruit.
  • Maraschino cherries: Add classic color and a touch of sweetness. Check the jar to find the brightest, plump cherries.
  • Cream cheese: Essential for a rich texture. Always soften it fully for a lump-free batter. Use full-fat for best results.
  • Granulated sugar: Provides just the right sweetness without overpowering the tang.
  • Sour cream: Introduces a subtle tang that balances the sugary topping. Choose full-fat for creaminess.
  • Vanilla extract: Enhances flavor throughout. Real extract always beats imitation for aroma and taste.
  • Eggs: Hold the batter together for a silky, sliceable cheesecake. Use fresh large eggs for even consistency.

Instructions

Prepare the Pan:
Set your oven to 325 F and line the bottom of your springform pan with parchment or a light coating of butter. Sprinkle brown sugar over the bottom so it is evenly covered. Arrange pineapple rings so they nearly touch and place one cherry at the center of each. Pour on the melted butter to moisten the sugar and fruit.
Build the Crust:
Combine graham cracker crumbs with more melted butter in a bowl. Mix until crumbs are evenly damp. Firmly press mixture on top of the pineapple layer in the pan so everything is snug. Freeze for at least ten minutes to set the crust.
Make the Cheesecake Batter:
In a large mixing bowl, beat the cream cheese and sugar together with a hand mixer or stand mixer until no lumps remain and the mixture turns fluffy. Crack the eggs in one by one, blending carefully after each so you do not whip in too much air.
Add Creamy Touches:
Blend in sour cream and vanilla extract by hand or on lowest mixer setting until smooth and glossy. Scrape down the sides as needed.
Fill and Smooth:
Gently pour the cheesecake filling over the pressed crust and fruit. Smooth the surface with an offset spatula for a level finish.
Bake Low and Slow:
Place the filled pan into a water bath inside your oven. The steam keeps your cheesecake velvety. Bake for around an hour until the outer edges are set and the very center still jiggles softly.
Cool Gradually:
Switch off the oven and crack the door open. Let the cheesecake relax inside the oven for one hour so it does not crack from a sudden temperature shift.
Chill and Set:
Remove the pan and slide it into the fridge for a minimum of four hours. Overnight is best for full flavor and firmness.
Release and Flip:
Run a thin knife around the inside edge of your pan to loosen the cheesecake. Release the pan sides and place a flat serving plate on top. Invert the pan and carefully lift away, revealing the caramelized fruit topping.
A slice of pineapple upside down cake.
A slice of pineapple upside down cake. | iamcooker.com

I always look forward to that first slice with the bright yellow pineapple and jewel red cherries on top. Sometimes we enjoy it as a summer birthday cake right off the patio table and it never disappoints.

Storage and Leftover Tips

Keep the cheesecake chilled in the fridge where it stays fresh for several days. Cover slices tightly with plastic so they do not absorb fridge odors. For clean slices every time, use a warm wet knife and wipe it between cuts.

Easy Ingredient Swaps

If you are out of graham crackers, vanilla wafers or simple digestive biscuits work well. Greek yogurt can substitute for sour cream in a pinch. Fresh pineapple will give even more flavor. If cherries are not your thing, thinly sliced strawberries look festive and taste great too.

Perfect Ways to Serve This

A dollop of whipped cream on each slice adds extra indulgence for a special occasion. For a tropical twist, sprinkle toasted coconut or chopped macadamias over the top right before serving. Small wedges work as a potluck treat, and leftovers make an amazing breakfast with coffee.

The Story Behind This Recipe

This recipe came about when I had only cheesecake ingredients and a can of pineapple rings in the pantry during a late-night baking mood. My kids thought the upside-down flip was magic. Since then, we look for reasons to make it for friends and neighbors.

Adapting for Every Season

Bright summer picnics and rainy winter weekends both call for this cheesecake. Try apple rings and cinnamon sugar in fall, or swap in cherries with almond extract in the spring.

A slice of cake with a slice missing.
A slice of cake with a slice missing. | iamcooker.com

This cheesecake is always a hit with friends and family. I hope you try it to bring some sunshine to your table soon.

Recipe Q&A

→ How do I prevent cracks in cheesecake?

Baking the cheesecake in a water bath helps maintain even heat and moisture, reducing the risk of cracks.

→ Can I use fresh pineapple?

Yes, fresh pineapple rings can replace canned for a brighter flavor and firmer texture.

→ Why invert the cheesecake?

Inverting reveals caramelized pineapple and cherries on top, making for an appealing presentation.

→ How do I know when the cheesecake is set?

The center should be slightly jiggly; it will finish setting as it cools in the oven and fridge.

→ What is the best way to serve this dessert?

Slice with a clean, warm knife for neat portions and enjoy chilled to highlight the flavors.

Pineapple Upside-Down Cheesecake

Pineapple, cherries, and creamy cheese atop a buttery graham base create a dreamy, nostalgic dessert.

Prep Duration
30 min
Cooking Period
70 min
Entire Time Required
100 min
Sofia Pitt: sofia


Difficulty: Moderate

Regional Style: American

Output: 12 Portions (One 9-inch cheesecake)

Dietary Attributes: Vegetarian

Needed Ingredients

→ Crust and Topping

01 1 1/2 cups graham cracker crumbs
02 1/2 cup unsalted butter, melted, divided
03 1/2 cup packed brown sugar
04 6 to 8 pineapple rings, canned or fresh, drained
05 6 to 8 maraschino cherries, drained

→ Filling

06 24 ounces cream cheese, softened
07 3/4 cup granulated sugar
08 1/2 cup sour cream
09 1 teaspoon vanilla extract
10 3 large eggs

Preparation Steps

Step 01

Preheat oven to 325°F (163°C). Grease a 9-inch springform pan. Sprinkle brown sugar evenly over the bottom. Arrange pineapple rings across the sugar and position a maraschino cherry in the center of each ring. Drizzle 1/4 cup melted butter over the fruit.

Step 02

Stir graham cracker crumbs with remaining 1/4 cup melted butter until well combined. Evenly press crust mixture over the pineapple layer. Place pan in freezer for 10 to 15 minutes to set.

Step 03

In a large mixing bowl, beat softened cream cheese with granulated sugar on medium speed until creamy and smooth, scraping sides as needed.

Step 04

Add eggs to cream cheese mixture one at a time, mixing on low speed after each addition just until combined, without overbeating.

Step 05

Blend in sour cream and vanilla extract until filling is fully combined and smooth.

Step 06

Pour cheesecake batter evenly over the chilled crust and pineapple layer in pan. Gently smooth surface with a spatula.

Step 07

Set springform pan into a larger roasting pan. Fill roasting pan with hot water halfway up the sides of the cheesecake pan. Bake for 60 to 70 minutes, until edges are set and center slightly jiggles.

Step 08

Turn off oven and crack door open. Allow cheesecake to cool slowly in oven for 1 hour.

Step 09

Remove from oven, cover, and refrigerate at least 4 hours or overnight until completely firm.

Step 10

Run a thin knife around the edge of pan to loosen. Release springform, carefully invert cheesecake onto serving platter so pineapple layer is facing up, then slice and serve.

Supplementary Details

  1. For clean slices, wipe the knife with a damp towel between cuts. Ensure all ingredients are at room temperature for a smoother filling.

Necessary Tools

  • 9-inch springform pan
  • Electric mixer
  • Large mixing bowl
  • Roasting pan for water bath
  • Rubber spatula

Allergen Advisory

Review each item for allergens. Consult a medical expert if unsure.
  • Contains dairy, eggs, and wheat (graham crackers).

Nutrient Breakdown (per serving)

This information is provided for reference and should not replace consultation with a health professional.
  • Caloric Value: 450
  • Total Fat: 28 g
  • Total Carbohydrate: 44 g
  • Proteins: 7 g