Pineapple Upside-Down Cheesecake

This show-stopping Pineapple Upside-Down Cheesecake brings together the nostalgic charm of pineapple-ring dessert with the rich, creamy indulgence of cheesecake. A layer of glazed pineapples and cherries sits beneath a silky cheesecake filling perched on a buttery graham-cracker crust — perfect for celebrations, special occasions, or when you simply want dessert to make an impression.

Why You’ll Love This Recipe

• A beautiful twist on two classics: pineapple upside-down and cheesecake.
• Juicy pineapple slices and maraschino cherries add colour, flavour and visual flair.
• Creamy cheesecake layer pairs elegantly with the caramelised fruit topping.
• Great for entertaining — elegant enough to serve guests, comforting enough for family.
• Make-ahead friendly: chilled cheesecake means minimal fuss when ready to serve.

Recipe Details

• Prep Time: ~30 minutes (plus chilling time)
• Bake Time: ~1 hour + cooling time
• Total Time: ~4–5 hours (including chilling)
• Yield: ~12 slices (from a 9-inch springform)
• Category: Dessert
• Method: Baked cheesecake
• Cuisine: American / Fusion
• Diet: Vegetarian (with dairy)
• Keywords: pineapple upside-down cheesecake, fruit cheesecake, show-stopping dessert

Ingredients You’ll Need

For the Pineapple Layer

• ¼ cup (≈ 60 g) unsalted butter, melted
• ½ cup (≈ 100 g) packed light or dark brown sugar
• 8–10 canned pineapple rings, drained and patted dry
• 8–10 maraschino cherries, drained
• 1 cup (≈ 110 g) graham cracker crumbs (for the crust layer above pineapple)
• 2 Tbsp granulated sugar

For the Cheesecake Layer

• 24 oz (≈ 675 g) full-fat cream cheese (room temperature)
• 1 cup (≈ 200 g) granulated sugar
• 3 Tbsp all-purpose flour
• ½ cup (120 g) sour cream (room temperature)
• ⅓ cup (≈ 80 ml) pineapple juice, reserved from the drained pineapple
• 2 tsp vanilla extract
• 3 large eggs, room temperature

Instructions

1. Prepare the Pan & Pineapple Layer

• Pre-heat the oven to 325 °F (163 °C). Grease a 9-inch springform pan and line the bottom with parchment.
• In a small bowl, combine the melted butter and brown sugar; spread this mixture evenly on the bottom of the springform pan.
• Arrange the pineapple rings over the butter-sugar layer, placing a cherry in the center of each ring.
• In another bowl, mix the graham cracker crumbs, granulated sugar and a little melted butter (if desired) and sprinkle or press gently over the pineapple layer to form a thin crust layer just above the fruit.

2. Make the Cheesecake Filling

• In a large mixing bowl (or stand mixer), beat the softened cream cheese until smooth. Add the granulated sugar and flour, mixing on low until combined.
• Add sour cream, pineapple juice and vanilla extract, mixing until smooth.
• Add the eggs one at a time, mixing on low speed after each until combined (avoid over-mixing to minimize air in the batter).
• Pour the cheesecake filling evenly over the pineapple/crumb layer in the pan.

3. Bake & Chill

• Place the springform pan in the oven and bake for approximately 55–65 minutes, or until the outer edges are set and the centre is slightly jiggly (it will firm up as it chills).
• After baking, turn off the oven and prop the door open; allow the cheesecake to cool in the oven for ~30 minutes. Then remove and allow to cool completely at room temperature. Finally, refrigerate (covered) for at least 4 hours, preferably overnight, until fully chilled and firm.

4. Unmould & Serve

• Run a knife around the edge of the pan to loosen, then remove the springform ring and invert the cheesecake onto a serving plate so that the pineapple rings are on top. (Alternatively: leave as is with pineapple visible above.)
• Slice into 12 pieces and serve chilled. Optionally garnish with whipped cream, extra cherries or a drizzle of caramel.

You Must Know

• Bring the cream cheese, sour cream and eggs to room temperature for smoother filling.
• Low-pace mixing avoids adding too much air—this helps prevent cracks.
• Chilling time is just as important as the bake time; the cheesecake will be soft if not fully chilled.
• Using quality pineapple (drained and patted dry) and cherries prevents excess moisture in the bottom layer.
• Running a knife around the side and chilling before removing the pan helps maintain clean edges.

Storage Tips

• Store in an airtight container in the fridge for up to 3–4 days.
• Leftover slices can be frozen (wrapped individually) for up to 2 months—thaw in refrigerator before serving.
• For best texture, serve chilled and let sit at room temperature ~10 minutes before eating.

Ingredient Substitutions

• Use crushed digestive biscuits or shortbread crumbs instead of graham crackers for the crust (fine in the UK/elsewhere).
• Replace sour cream with full-fat Greek yogurt (same amount) for a slightly tangier flavour.
• For a lighter version, reduce sugar by ~¼ cup (note: sweetness level will drop).
• Use fresh pineapple rings (if in season) — pat dry thoroughly and brush lightly with melted butter-sugar before layering.

Serving Suggestions

• Serve alongside a scoop of vanilla ice cream or dollop of whipped cream to contrast the slightly tangy cheesecake.
• Pair with fresh berries (such as raspberries or blueberries) to add bright flavour and colour.
• For a tropical twist, serve with toasted coconut flakes or pineapple sorbet.
• Present in an elegant dessert spread for dinner parties—its decorative pineapple rings make a visual statement.

Pro Tips

• Use a springform pan with a removable bottom for easiest inversion.
• Double-wrap the pan with foil if using a water bath to prevent leaks (helps with even baking).
• When cutting slices, wipe the knife blade with a warm dry cloth between cuts to keep edges neat.
• If cracks form on top, cover with a thin layer of whipped cream or pineapple compote to mask.

Frequently Asked Questions

→ Can I skip the pineapple rings and just have pineapple chunks?
Yes—arrange pineapple chunks instead of rings; the appearance will differ slightly but the flavour remains delightful.
→ Why did my cheesecake crack?
Common causes: over-mixing (too much air), oven temperature too high, baking time too long, or skipping cooling steps.
→ Can I make it ahead for a party?
Definitely — bake the day before, chill overnight, then invert and serve the next day for stress-free dessert time.

→ Is this dessert suitable for vegetarian diet?
Yes — it contains no gelatin or other animal-derived ingredients (aside from dairy), so it’s appropriate for vegetarians who consume dairy. For a vegan version, use vegan cream cheese and yogurt, and ensure crust and pineapple layer are vegan-friendly.

✨ This Pineapple Upside-Down Cheesecake brings tropical sweetness, creamy indulgence and show-stopping presentation to your dessert table—treat yourself and your guests to something special.

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