These Pineapple Upside Down Sugar Cookies are a tropical twist on a classic treat, combining soft, chewy sugar cookie dough with the caramelized flavor of pineapple and the sweetness of maraschino cherries. They’re everything you love about pineapple upside-down cake—reimagined into handheld cookies. Each one is topped with a golden pineapple ring and a bright cherry center, giving it a fun, vintage look that’s both eye-catching and delicious.
Perfect for parties, bake sales, or summertime gatherings, these cookies bake up beautifully and offer a refreshing burst of fruitiness in every bite. The cookie base is buttery and sweet, while the pineapple topping creates a juicy contrast that’s hard to resist. A sprinkle of brown sugar on top creates a hint of caramelization in the oven, making these cookies smell and taste just like a slice of sunshine.
Why You’ll Love This Recipe
• Combines a classic sugar cookie with fruity topping
• Soft, buttery texture with crisp golden edges
• Eye-catching presentation with minimal effort
Ingredients
1 cup unsalted butter, softened
1 cup granulated sugar
½ cup brown sugar
2 large eggs
1 teaspoon vanilla extract
3 cups all-purpose flour
1 teaspoon baking powder
½ teaspoon salt
24 maraschino cherries
24 pineapple rings, drained
¼ cup light brown sugar (for topping)
Instructions
Step 1: Preheat the Oven
Preheat your oven to 350°F (175°C).
Line a large baking sheet with parchment paper or a silicone baking mat.
Step 2: Cream the Butter and Sugars
In a large bowl, cream together the softened butter, granulated sugar, and brown sugar using a mixer on medium speed.
Beat until the mixture is light and fluffy, about 2–3 minutes.
Step 3: Add the Eggs and Vanilla
Add the eggs one at a time, beating well after each addition.
Stir in the vanilla extract until fully incorporated.
Step 4: Mix the Dry Ingredients
In a separate bowl, whisk together the flour, baking powder, and salt.
Gradually add the dry mixture to the butter mixture, mixing just until a soft dough forms.
Step 5: Shape the Cookies
Roll the dough into 1-inch balls and place them on the prepared baking sheet, spacing them about 2 inches apart.
Flatten each dough ball slightly with your fingers or the bottom of a glass.
Step 6: Add the Pineapple and Cherry
Gently press a pineapple ring on top of each dough ball.
Place a maraschino cherry in the center of each pineapple ring.
Sprinkle a pinch of light brown sugar over the top of each assembled cookie for a caramelized effect.
Step 7: Bake
Bake in the preheated oven for 12–15 minutes, or until the edges of the cookies are golden brown and the pineapples are lightly caramelized.
Step 8: Cool and Serve
Let the cookies cool on the baking sheet for 5 minutes before transferring to a wire rack.
Allow them to cool completely before serving so the fruit sets properly.
Tips for Success
• Pat the pineapple rings dry with paper towels to reduce excess moisture
• Use a cookie scoop for even portioning of dough
• Rotate the baking sheet halfway through baking for even browning
Storage Options
Store in an airtight container at room temperature for up to 3 days
Refrigerate for longer shelf life (up to 1 week)
Freeze the unbaked dough balls and top with pineapple/cherry just before baking for make-ahead convenience
