Pineapple Upside Sugar Cookies
These Pineapple Upside Sugar Cookies combine the nostalgic flavors of pineapple upside-down cake with a soft, chewy sugar cookie base. With crushed pineapple, coconut, and a caramelized brown sugar coating, they’re a tropical twist perfect for sunny days, bake sales, or festive treats.
Prep Time 15 minutes mins
Cook Time 15 minutes mins
Servings 24 cookies
Calories 180 kcal
- 1 cup unsalted butter softened
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 2½ cups all-purpose flour
- ½ teaspoon baking powder
- ¼ teaspoon salt
- ½ cup crushed pineapple well-drained
- ½ cup brown sugar for rolling
- ¼ cup unsweetened shredded coconut
- Maraschino cherries optional, for garnish
Preheat oven to 350°F (175°C). Line two baking sheets with parchment paper.
In a large bowl, cream butter and sugar until light and fluffy (2–3 minutes).
Beat in egg and vanilla until smooth.
In another bowl, whisk flour, baking powder, and salt.
Gradually mix dry ingredients into wet until just combined.
Fold in drained pineapple and shredded coconut.
In a small bowl, mix brown sugar with 1–2 teaspoon flour.
Roll dough into tablespoon-sized balls and coat in brown sugar mixture.
Place on baking sheets, flatten slightly, and add a maraschino cherry to each (if using).
Bake for 12–15 minutes, until edges are golden.
Cool on sheet for 5 minutes, then transfer to wire rack to cool completely.
-
Drain pineapple well to avoid soggy dough.
-
Substitute lime zest for a citrusy boost.
-
For crunch, toast the coconut beforehand.
-
Freeze dough balls for later; bake from frozen with 1–2 extra minutes.
-
For a decorative finish, drizzle with pineapple glaze (powdered sugar + pineapple juice).