Pineapple Upside Down Sugar Cookie Recipe – Easy Tropical Dessert
This Pineapple Upside Down Sugar Cookie Recipe is a fun twist on the classic cake. Featuring a buttery sugar cookie base topped with caramelized pineapple rings and maraschino cherries, it delivers tropical sweetness in every bite. Easy to prepare and visually stunning, this dessert is perfect for parties, holidays, or whenever you want a treat that’s both nostalgic and unique. With its chewy cookie texture and fruity topping, it’s a delightful recipe that will impress family and friends.
Equipment
- Muffin pan (12 cups) or mini muffin pan for bite-sized cookies
- Parchment liners or nonstick spray
- Mixing bowls
- Hand or stand mixer
- Whisk or spoon
- Cooling rack
- Measuring Cups and Spoons
Ingredients
For the Topping:
- 3 tbsp unsalted butter, melted
- 1/4 cup brown sugar
- 12 pineapple slices or chunks, well-drained
- 12 maraschino cherries, drained
For the Cookie Dough:
- 1/2 cup unsalted butter, softened
- 1/2 cup granulated sugar
- 1 large egg
- 1 tsp vanilla extract
- 1 1/4 cups all-purpose flour
- 1/2 tsp baking powder
- 1/4 tsp salt
- Optional: 1/2 tsp cinnamon or ginger for spice
- Optional: 1/4 cup shredded coconut
Instructions
- Prep Oven & Pan: Preheat oven to 350°F (175°C). Line muffin tins with parchment or lightly grease.
- Make Brown Sugar Topping: Mix melted butter and brown sugar. Spoon about 1 tsp into each muffin cup.
- Prep Fruit: Place a drained pineapple piece and a cherry on top of each brown sugar portion.
- Make Cookie Dough: Cream butter and sugar until light. Add egg and vanilla, mix until combined. Fold in dry ingredients gently. Add optional spices or coconut if desired.
- Assemble Cookies: Spoon dough over fruit, smoothing lightly so fruit is just covered or peeking.
- Bake: 12–15 minutes until edges are lightly golden. Avoid overbaking.
- Cool & Flip: Let cookies rest briefly, then invert onto a cooling rack to reveal caramelized fruit tops. Cool completely before serving
Notes
- Drain Fruit Well: Excess pineapple juice makes cookies soggy. Pat dry before assembling.
- Optional Spices: Cinnamon, nutmeg, or ginger enhance depth of flavor.
- Mini Cookie Cups: Use mini muffin pans for bite-sized treats.
- Storage: Store in an airtight container at room temperature up to 3 days; refrigerate up to a week.
- Serving Suggestion: Slightly warm with ice cream or whipped cream for extra indulgence.
- Creative Variations: Fold shredded coconut into dough, or swap pineapple with mango or peach for seasonal flair.