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Pineapple Upside Down Cookies Recipe

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3.9 from 60 reviews

Sweet and juicy Pineapple Upside Down Cookies featuring a soft sugar cookie base topped with a pineapple ring and maraschino cherry. These individual portions mimic the classic pineapple upside-down cake, making them perfect for parties or any special occasion.

  • Total Time: 24 minutes
  • Yield: 12 cookies

Ingredients

Cookie Ingredients

  • ½ cup Butter, softened
  • ½ cup Granulated Sugar (100g)
  • 1 Large Egg
  • 1 teaspoon Vanilla Extract
  • ½ cup Powdered Sugar (65g)
  • ¼ cup Vegetable Oil
  • ½ teaspoon Baking Soda
  • ½ teaspoon Cream of Tartar
  • 2 cups All Purpose Flour (240g)

Pineapple Topping

  • Pineapple Rings, drained
  • Maraschino Cherries, drained
  • 6 tablespoons Butter, melted
  • 1 cup Brown Sugar (214g)

Instructions

  1. Prepare the Pan: Preheat your oven to 350°F (177°C). In a small mixing bowl, combine ½ cup melted butter with 1 cup brown sugar, stirring until well blended. Drain the pineapple rings thoroughly and set aside.
  2. Assemble Topping in Muffin Tin: Place 1 tablespoon of the brown sugar butter mixture into each well of a muffin tin. Top each with a pineapple ring, then place a maraschino cherry in the center of each ring. To prevent cookies from sticking to each other as they spread, stagger their positioning in the pan.
  3. Make Cookie Dough: In a mixing bowl, cream together softened butter and granulated sugar until light and fluffy, scraping the sides as needed. Add the egg and vanilla extract, continuing to cream for 2-3 minutes. Gradually mix in vegetable oil and powdered sugar until the mixture is pale yellow and smooth.
  4. Add Dry Ingredients: Gently fold in all-purpose flour, baking soda, and cream of tartar until the dough is fully combined without overmixing.
  5. Shape and Place Dough: Using a #24 cookie scoop, portion out the dough. Flatten each scoop into approximately 3-inch diameter discs with the palm of your hand. Carefully place each flattened dough disc on top of the pineapple ring and cherry in the muffin tin well. Press the dough into the sides of the pan to seal the edges.
  6. Bake: Bake the cookies at 350°F (177°C) for 8-10 minutes, or until the edges turn lightly golden and the centers are no longer glossy.
  7. Invert and Cool: Remove the muffin tin from the oven and immediately flip it onto a parchment-lined cookie sheet. The cookies will release from the tins, revealing their iconic upside-down pineapple design. Allow cookies to cool completely before serving.

Notes

  • Ensure pineapple rings are well drained to avoid soggy cookie bottoms.
  • Staggering cookie placement in the pan helps prevent them from merging during baking.
  • Use room temperature butter for easier creaming and better cookie texture.
  • Cooling the cookies on the parchment before serving helps them set and enhances flavor.
  • These cookies can be stored in an airtight container at room temperature for up to 4 days.
  • Author: ELLA
  • Prep Time: 15 minutes
  • Cook Time: 9 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Find it online: https://ellarecipe.com/pineapple-upside-down-cookies-recipe/