Description
Pineapple Upside Sugar Cookies are a tropical twist on the classic upside-down cake—soft, buttery sugar cookies topped with golden caramelized pineapple and a bright cherry. They’re crisp at the edges, gooey in the center, and bring all the sunny vibes! Perfect for summer parties, bake sales, or anytime you need a little edible sunshine.
Ingredients
For the Topping:
6 pineapple rings, cut in half
12 maraschino cherries
¼ cup brown sugar
2 tablespoons butter, melted
For the Cookie Dough:
½ cup butter, softened
½ cup granulated sugar
½ cup brown sugar
1 large egg
1 teaspoon vanilla extract
1½ cups all-purpose flour
½ teaspoon baking soda
¼ teaspoon salt
Instructions
Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper or a silicone mat.
Make the cookie dough: In a bowl, cream the softened butter with granulated sugar and brown sugar until fluffy. Beat in the egg and vanilla. Stir in flour, baking soda, and salt just until combined. Set aside.
Prepare the topping: In a small bowl, mix brown sugar and melted butter. Spoon 1 teaspoon of this mixture onto the baking sheet for each cookie. Top each spot with half a pineapple ring and a maraschino cherry in the center.
Assemble the cookies: Scoop about 2 tablespoons of dough and place on top of each fruit-topped spot. Gently flatten the dough just a bit.
Bake for 12–14 minutes or until the edges are golden and the centers are set. Let cookies cool on the tray for 5 minutes.
Flip carefully using a spatula to reveal the caramelized pineapple topping. Transfer to a cooling rack and let cool completely.
Notes
Dry your pineapple well with paper towels to prevent excess moisture from affecting the cookie texture.
Use parchment or a silicone mat—the caramel can stick to bare pans.
Add-ins like shredded coconut or a splash of rum extract take these cookies to the next level.
Store at room temp for up to 3 days or in the fridge for 5 days. The dough can be made ahead and refrigerated overnight.
These are best the day they’re baked, when the caramel is still slightly sticky and the cookies are soft and fresh!