These pineapple upside-down sugar cookies bring sweet island vibes to your dessert table! With a soft sugar cookie base, caramelized crushed pineapple, and a cherry on top, they’re a fun twist on the beloved retro cake. Perfect for summer gatherings, potlucks, or whenever you want a cheerful, fruity cookie that’s as cute as it is delicious.
1½ cups all-purpose flour
½ tsp baking soda
¼ tsp salt
½ cup unsalted butter, softened
1 cup granulated sugar
1 large egg
1 tsp vanilla extract
¼ cup crushed pineapple (drained)
½ cup light brown sugar (packed)
12 maraschino cherries (or pineapple rings for topping)
Preheat oven to 350°F (175°C) and line a baking sheet with parchment paper.
In a medium bowl, whisk together flour, baking soda, and salt. Set aside.
In a large bowl, beat softened butter and sugar until creamy. Add egg and vanilla; mix until smooth.
Gradually stir in the dry ingredients to form a soft dough.
Scoop 1 tbsp-sized portions, roll into balls, and place on the baking sheet.
Mix brown sugar with crushed pineapple. Spoon a little on top of each dough ball.
Gently press a maraschino cherry (or small pineapple ring) into the center.
Bake for 12–15 minutes, or until edges are golden.
Let cool on the pan a few minutes before moving to a wire rack.