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Pineapple Upside Down Sugar Cookies

A soft and chewy sugar cookie topped with a caramelized pineapple ring and maraschino cherry, mimicking the classic cake flavors.
Prep Time 15 minutes
Cook Time 12 minutes
Total Time 35 minutes
Servings: 12 cookies
Course: Dessert, Snack
Cuisine: American, Tropical
Calories: 185

Ingredients
  

Cookie Dough
  • 0.5 cup unsalted butter softened
  • 0.5 cup granulated sugar
  • 0.25 cup light brown sugar packed
  • 1 egg large, room temp
  • 1 tsp vanilla extract
  • 1.5 cups all-purpose flour
  • 0.5 tsp baking powder
  • 0.25 tsp baking soda
  • 0.25 tsp salt
Toppings
  • 12 slices canned pineapple rings drained well and patted dry
  • 12 maraschino cherries
  • 2 tbsp butter melted
  • 2 tbsp brown sugar for sprinkling/glazing

Equipment

  • Baking sheets
  • Parchment paper
  • Stand mixer or hand mixer
  • Wire cooling rack

Method
 

  1. Preheat oven to 350°F (175°C). Line two large baking sheets with parchment paper.
  2. Remove pineapple rings from can and lay them on paper towels. Press firmly to remove as much moisture as possible.
  3. In a large bowl, cream together softened butter, granulated sugar, and brown sugar until light and fluffy.
  4. Beat in the egg and vanilla extract until smooth.
  5. In a separate bowl, whisk together flour, baking powder, baking soda, and salt. Gradually add to wet ingredients, mixing until just combined.
  6. Scoop dough into balls and place on prepared baking sheets, spacing them 3 inches apart.
  7. Flatten each dough ball slightly, then press a dried pineapple ring into the center of each.
  8. Place a maraschino cherry in the center of each pineapple ring.
  9. Brush the pineapple tops with melted butter and sprinkle with a little extra brown sugar.
  10. Bake for 10-12 minutes until edges are golden brown. Cool on baking sheet for 5 minutes, then transfer to wire rack.

Notes

Ensure pineapple is very dry to prevent soggy cookies.