Introduction

Pineapple Upside Sugar Cookies are a delightful twist on the classic pineapple upside-down cake.
These cookies combine the tropical sweetness of pineapple with the buttery flavor of traditional sugar cookies.
Topped with caramelized brown sugar and a cherry, each bite brings a soft, chewy texture with a burst of fruity flavor —
perfect for parties, holidays, or simply a sweet treat any day.

Ingredients

For the Topping:

• 1 cup crushed pineapple (drained)
• ¼ cup brown sugar
• 2 tablespoons unsalted butter
• 10–12 maraschino cherries (halved)

For the Cookie Dough:

• 2 ½ cups all-purpose flour
• ½ teaspoon baking powder
• ¼ teaspoon baking soda
• ¼ teaspoon salt
• ¾ cup unsalted butter (softened)
• 1 cup granulated sugar
• 1 large egg
• 1 teaspoon vanilla extract
• 1 tablespoon pineapple juice (from the can)

Instructions

1. Preheat your oven to 350°F (175°C) and line a muffin tin or baking sheet with parchment paper.
2. In a small saucepan, melt the butter over medium heat. Stir in the brown sugar until dissolved. Spoon about ½ teaspoon of the mixture into each muffin cup or onto parchment paper in small circles.
3. Place a small spoonful of crushed pineapple on top of each sugar-butter base and add half a cherry in the center.
4. In a bowl, whisk together flour, baking powder, baking soda, and salt. In a separate large bowl, beat butter and sugar until creamy. Add egg, vanilla, and pineapple juice; mix until smooth. Gradually add the dry ingredients to form a soft dough.
5. Roll dough into balls (about 1½ tablespoons each) and flatten slightly. Place them gently on top of the pineapple mixture.
6. Bake for 12–15 minutes, or until edges are lightly golden. Let cool for 5 minutes, then carefully invert onto a wire rack to reveal the pineapple topping.
7. Allow cookies to cool completely before serving.

Description

These cookies are soft, buttery, and packed with tropical charm. The caramelized pineapple and cherry topping add a beautiful golden finish,
while the cookie base remains light and chewy. It’s like a bite-sized version of pineapple upside-down cake — nostalgic, fun, and irresistibly delicious.

Tips

• Drain the pineapple well to prevent soggy cookies.
• Use a nonstick muffin pan for the neatest upside-down look.
• Add a pinch of cinnamon or nutmeg for extra warmth.
• Store in an airtight container for up to 3 days — they taste even better the next day!
• For an elegant presentation, top each cookie with a drizzle of glaze or a sprinkle of toasted coconut.

Correction

• If cookies turn out too soft or crumbly, measure the flour correctly — spoon and level it.
• If the dough is too sticky, chill it for 30 minutes before baking.
• If the topping burns, lower your oven temperature slightly or bake on the middle rack.