Pineapple Upside Down Sugar Cookies (Printable Version)
Soft sugar cookies with caramelized pineapple and cherry toppings for a bite-sized tropical treat.
# Ingredient List:
→ Fruit Topping
01 - 1 cup pineapple, diced (fresh or canned, well drained)
02 - 9 maraschino cherries, halved
03 - 3 tablespoons unsalted butter, melted
04 - 1/3 cup light brown sugar
→ Sugar Cookie Dough
05 - 2 1/4 cups all-purpose flour
06 - 1/2 teaspoon baking powder
07 - 1/4 teaspoon salt
08 - 3/4 cup unsalted butter, softened
09 - 1 cup granulated sugar
10 - 1 large egg
11 - 1 teaspoon vanilla extract
# How to Make:
01 - Preheat oven to 350°F. Line two large baking sheets with parchment paper.
02 - In a small bowl, combine melted butter and brown sugar until well blended.
03 - Place a teaspoon of the butter-sugar mixture in the center of each parchment-lined cookie spot (18 spots total, spaced apart).
04 - Arrange a few pineapple pieces and half a cherry over each butter-sugar mound, pressing gently to adhere.
05 - In a medium bowl, whisk together flour, baking powder, and salt until uniform.
06 - In a large bowl, cream softened butter and granulated sugar until light and fluffy. Add egg and vanilla; beat until fully combined.
07 - Gradually add the dry ingredients to the wet mixture, mixing just until a soft dough forms. Avoid overmixing.
08 - Scoop 2-tablespoon portions of dough and flatten into thick discs. Place each disc over the pineapple-cherry topping, ensuring the fruit is completely covered.
09 - Bake for 13–15 minutes, until edges are lightly golden and centers are set.
10 - Let cool on the sheet for 3 minutes, then carefully invert each cookie onto a wire rack while still warm to reveal the caramelized fruit topping.
11 - Allow cookies to cool completely before serving to achieve optimal texture.
# Expert Tips:
01 -
- That moment of flipping warm cookies to reveal the glistening fruit topping feels like a tiny kitchen miracle every single time
- The caramelized pineapple and cherries turn simple sugar cookies into something that tastes like effort even though they come together in under an hour
02 -
- Timing matters when flipping wait 3 minutes after baking but no longer or the caramel hardens and the fruit sticks to the parchment
- Press the dough edges down firmly to create a seal otherwise the butter sugar mixture will bubble out and create a sticky mess in your oven
03 -
- If your pineapple is extra juicy give those chunks a quick squeeze or pat them dry before arranging them on the caramel
- Use a small offset spatula to gently lift and flip the cookies it gives you way more control than your fingers ever could