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A close-up macro shot of Pineapple Upside Down Cookies stacked on a simple ceramic plate, showing the rich, moist texture and glistening pineapple topping. (Pineapple Upside Down Cookies)

Pineapple Upside Down Cookies: The Ultimate Gooey & Golden Treat

This Pineapple Upside Down Cookies recipe guides you to make a show-stopping dessert featuring a gooey brown sugar cookie base, a glistening caramelized pineapple ring, and a bright maraschino cherry. A nostalgic classic transformed into a perfect handheld treat.
Prep Time 20 minutes
Cook Time 15 minutes
Total Time 35 minutes
Servings: 12 cookies
Course: Dessert
Cuisine: American
Calories: 210

Ingredients
  

  • 1/4 cup (57g) unsalted butter, melted
  • 1/2 cup (110g) light brown sugar, packed
  • 12 canned pineapple rings in juice, drained well
  • 12 maraschino cherries, drained and patted dry
  • 1 1/2 cups (180g) all-purpose flour
  • 1/2 tsp baking soda
  • 1/4 tsp fine sea salt
  • 1/2 cup (113g) unsalted butter, softened to room temperature
  • 1/4 cup (50g) granulated sugar
  • 1/4 cup (55g) light brown sugar, packed
  • 1 large egg, at room temperature
  • 1 tsp pure vanilla extract

Equipment

  • 1 12-cup muffin tin
  • 1 Electric mixer
  • 1 Wire Cooling Rack

Method
 

  1. Preheat oven to 350°F (175°C). In a small bowl, combine the 1/4 cup of melted butter and 1/2 cup of brown sugar. Divide this mixture evenly among 12 standard-sized muffin cups.
  2. Pat the pineapple rings and maraschino cherries completely dry. Place one pineapple ring into each muffin cup, pressing it gently into the sugar mixture. Place a cherry in the center of each ring.
  3. In a medium bowl, whisk together the all-purpose flour, baking soda, and salt. Set aside.
  4. In a large bowl using an electric mixer, beat the 1/2 cup of softened butter with the granulated sugar and 1/4 cup of brown sugar until light and fluffy, about 2-3 minutes.
  5. Beat in the egg and vanilla extract until just combined. Gradually add the dry flour mixture to the wet ingredients, mixing on low speed until a soft dough forms.
  6. Scoop about 1.5 tablespoons of cookie dough on top of each pineapple ring, spreading it gently to cover the fruit.
  7. Bake for 12-15 minutes, or until the edges are golden brown. Let the pan cool on a wire rack for exactly 5 minutes, then carefully invert the cookies onto parchment paper.

Notes

Don't overbake the cookies to ensure a gooey center.
The 5-minute cooling period before inverting is critical to prevent sticking.
Ensure your pineapple and cherries are patted very dry to avoid a watery caramel.
Use room temperature butter and egg for the best cookie dough texture.