Ingredients
For the Pineapple Topping
½ cup (100g) light brown sugar, packed
4 Tbsp (57g) unsalted butter
12–14 maraschino cherries
1 cup crushed pineapple, well-drained
Optional: ½ tsp vanilla extract or ¼ tsp rum extract
For the Graham Cracker Crust
1 ¼ cups (140g) graham cracker crumbs
3 Tbsp (40g) granulated sugar
5 Tbsp (70g) unsalted butter, melted
Pinch of salt
For the Cheesecake Batter
16 oz (450g) cream cheese, softened to room temperature
½ cup (100g) granulated sugar
2 large eggs, room temperature
½ cup (120g) sour cream, room temperature
1 tsp vanilla extract
1 Tbsp all-purpose flour (helps prevent cracking)
Optional: 1 Tbsp pineapple juice (from drained pineapple)
Special Equipment
Standard 12-cup muffin pan
Paper liners (foil-lined work best)
Hand mixer or stand mixer
Mixing bowls
Small saucepan
Cookie scoop or spoon
Step-by-Step Instructions
STEP 1 — Prep
Preheat your oven to 325°F (163°C).
Line a muffin pan with foil or parchment paper liners (regular thin paper liners may get soggy from the topping).
STEP 2 — Make the Pineapple Upside-Down Topping
In a small saucepan, melt 4 Tbsp butter over medium heat.
Add ½ cup brown sugar and stir constantly until the sugar dissolves and the mixture becomes glossy and bubbling (about 2 minutes).
Remove from heat and stir in vanilla or rum extract (optional).
Spoon about 1 teaspoon of the brown sugar mixture into the bottom of each liner.
Add 1 maraschino cherry to the center of each.
Place 1–2 teaspoons of crushed pineapple around the cherry, flattening it gently with the back of a spoon.
Tip: Be sure the pineapple is well-drained so the cheesecakes don’t become soggy.
STEP 3 — Make the Graham Cracker Crust
Combine graham cracker crumbs, sugar, salt, and melted butter until everything looks like wet sand.
Spoon about 1 tablespoon of crust mixture over the pineapple in each liner.
Press down firmly with the back of a spoon or a small glass.
Tip: Firm packing helps keep the crust from crumbling when you unmold the cheesecakes.
STEP 4 — Make the Cheesecake Filling
In a large bowl, beat cream cheese until smooth and fluffy (30–45 seconds).
Add sugar and mix until completely combined.
Add eggs one at a time, mixing on low speed just until incorporated (do not overbeat).
Add sour cream, vanilla, and flour, mixing on low speed.
Fold in 1 tbsp pineapple juice if using.
Your batter should be silky and lump-free.
STEP 5 — Assemble
Spoon the cheesecake batter into each muffin cup, filling each about ¾ full.
STEP 6 — Bake
Bake at 325°F for 22–28 minutes, or until:
centers are slightly jiggly like Jell-O
edges look set
Do not overbake or the cheesecake will crack.
STEP 7 — Cool and Chill
Let the cheesecakes cool in the pan for 30–45 minutes.
Transfer to the refrigerator and chill at least 3–4 hours, or overnight for best texture.
STEP 8 — Unmold and Serve
Once fully chilled, remove the liners.
Flip each cheesecake upside down to reveal the pineapple and cherry topping.
Spoon any pooled brown sugar mixture from the bottom of the liner over the top.
Optional Add-Ons and Variations
- Coconut-Pineapple Cheesecakes
Add ¼ cup shredded coconut to the crust or sprinkle on top before baking.
- Pina Colada Cheesecakes
Add 1–2 tsp rum extract to the cheesecake batter.
Use toasted coconut as a garnish.
- Cake-Layer Cheesecakes
Add a thin slice of pound cake under the crust before baking for a more traditional upside-down cake texture.
- Gluten-Free Version
Replace graham crackers with gluten-free cookie crumbs.
Storage
Fridge: Up to 5 days in an airtight container.
Freezer: Freeze for up to 2 months. Thaw overnight in the fridge.