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Close-up of freshly baked pineapple cookies topped with pineapple rings, red cherries, and green sugar leaves.

Pineapple Upside Down Sugar Cookies

These delightful pineapple upside down sugar cookies combine the classic buttery sweetness of a sugar cookie with the caramelized pineapple and cherry charm of the iconic dessert. Each bite offers a perfect balance of soft cookie, sticky-sweet pineapple, and a hint of bright cherry.
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Prep Time 45 minutes
Cook Time 30 minutes
Total Time 1 hour 15 minutes
Servings: 24 cookies
Course: Dessert, Snack
Cuisine: American
Calories: 200
Ingredients Equipment Method Notes

Ingredients
  

For the Pineapple Topping
  • 1/4 cup unsalted butter melted
  • 1/2 cup light brown sugar packed
  • 1 can (8 oz) crushed pineapple well-drained
  • 12 maraschino cherries halved (or 24 whole, if preferred)
For the Cookie Dough
  • 2 1/4 cups all-purpose flour
  • 1 tsp baking powder
  • 1/2 tsp salt
  • 1 cup (2 sticks) unsalted butter room temperature
  • 1 1/2 cups granulated sugar
  • 2 large eggs room temperature
  • 1 tsp vanilla extract

Equipment

  • Large mixing bowls
  • Electric mixer (stand or hand-held)
  • Measuring cups and spoons
  • Rolling Pin
  • 2.5-inch round cookie cutter
  • Small saucepan
  • Baking Sheets
  • Parchment Paper or Silicone Baking Mats
  • Wire cooling rack

Method
 

Prepare the Pineapple Topping
  1. In a small saucepan, melt the butter over medium heat. Add the brown sugar and stir until it dissolves and forms a thick, syrupy caramel. Remove from heat and set aside to cool slightly.
  2. In a small bowl, combine the well-drained crushed pineapple with the halved maraschino cherries. Set aside.
Make the Cookie Dough
  1. In a medium bowl, whisk together the flour, baking powder, and salt. Set aside.
  2. In a large mixing bowl, cream together the softened butter and granulated sugar with an electric mixer until light and fluffy (about 2-3 minutes).
  3. Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
  4. Gradually add the dry ingredients to the wet ingredients, mixing on low speed until just combined. Do not overmix.
  5. Divide the dough in half, flatten each half into a disc, wrap tightly in plastic wrap, and refrigerate for at least 30 minutes (or up to 1 hour) to firm up. This makes the dough easier to handle.
Assemble and Bake
  1. Preheat oven to 375°F (190°C). Line two baking sheets with parchment paper or silicone mats.
  2. On a lightly floured surface, roll out one disc of chilled cookie dough to about 1/4-inch thickness. Use a 2.5-inch round cookie cutter to cut out cookies. Reroll scraps as needed.
  3. Carefully spoon about 1/2 teaspoon of the slightly cooled brown sugar caramel onto the center of each cutout cookie on the baking sheet.
  4. Top the caramel with a small amount (about 1 teaspoon) of the pineapple and cherry mixture, pressing down gently.
  5. Bake for 10-12 minutes, or until the edges are lightly golden and the cookies are set. The caramel topping will be bubbly.
  6. Let the cookies cool on the baking sheets for 5 minutes before carefully transferring them to a wire rack to cool completely. The topping will firm up as it cools. Repeat with remaining dough and topping.

Notes

Store pineapple upside down sugar cookies in an airtight container at room temperature for up to 3 days. For best results, consume within 1-2 days to enjoy the topping at its freshest. If the dough gets too warm during rolling, place it back in the refrigerator for 10-15 minutes. Ensure the crushed pineapple is very well drained to prevent the cookies from becoming soggy.