Pineapple Upside Sugar Cookies are a fun twist on the classic pineapple upside-down cake — but in cookie form. Buttery sugar cookies are topped with sweet pineapple rings and bright maraschino cherries, creating a soft, fruity dessert that’s colorful and nostalgic.
They’re perfect for spring gatherings, summer parties, bake sales, or whenever you want something cheerful and different.
Yield and Timing
Makes 18–24 cookies
Prep time: 15 minutes
Bake time: 12–15 minutes
Ingredients
- 1 package refrigerated sugar cookie dough (or homemade sugar cookie dough)
- 1 can pineapple rings, drained and patted dry
- Maraschino cherries, halved
- ¼ cup brown sugar
- 2 tablespoons melted butter
Preparation
Preheat oven to 350°F (175°C). Lightly grease a muffin tin or line with parchment.
In a small bowl, mix brown sugar and melted butter.
Spoon about 1 teaspoon of the brown sugar mixture into the bottom of each muffin cup.
Cut pineapple rings into small pieces that fit inside each muffin cup. Place pineapple pieces over the brown sugar layer.
Place half a cherry in the center of each pineapple piece.
Press a scoop of sugar cookie dough (about 1–2 tablespoons) over the pineapple layer, gently flattening to cover.
Bake for 12–15 minutes, until the cookie is golden brown.
Allow to cool for about 5 minutes, then carefully invert onto a tray while still warm.
Serving Suggestions
Serve warm or at room temperature. These cookies pair beautifully with:
- Coffee
- Vanilla ice cream
- Whipped cream
Storage
Store in an airtight container in the refrigerator for up to 4 days due to the fruit topping.
Why These Cookies Are So Popular
They combine the buttery softness of sugar cookies with the sweet-tart flavor of pineapple and cherry. The caramelized brown sugar layer adds extra richness, making every bite soft, fruity, and slightly sticky — just like the classic cake.
Pineapple Upside Sugar Cookies are playful, colorful, and guaranteed to stand out on any dessert table.
Enjoy !!!
