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Pineapple Upside-Down Sugar Cookies

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These Pineapple Upside-Down Sugar Cookies combine the nostalgic charm of a classic pineapple upside-down cake with the soft, buttery goodness of sugar cookies. Each cookie features a caramelized pineapple ring and cherry on top—beautiful, bright, and irresistibly delicious.

  • Author: Sophia
  • Prep Time: 15 minutes
  • Cook Time: 12–15 minutes
  • Total Time: 35–40 minutes
  • Yield: 8–10 large cookies
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Ingredients

  • 4 tbsp butter (for topping)
  • 1/2 cup brown sugar
  • 8–10 pineapple rings, well drained
  • 8–10 maraschino cherries
  • 1/2 cup butter, softened (for dough)
  • 1 cup granulated sugar
  • 1 egg
  • 2 tsp vanilla extract
  • 1 1/2 cups all-purpose flour
  • 1/2 tsp baking soda
  • 1/4 tsp baking powder
  • 1/4 tsp salt

Instructions

  1. Preheat oven to 350°F (175°C) and line a large baking sheet with parchment paper. Lightly grease the parchment to prevent sticking.
  2. Melt 4 tbsp butter in a small saucepan. Stir in 1/2 cup brown sugar and cook until bubbly and thick, about 1 minute.
  3. Spoon 1 1/2–2 teaspoons of caramel mixture onto the parchment paper for each cookie. Place a pineapple ring on top of each caramel puddle and add a maraschino cherry to the center of each ring.
  4. In a large bowl, cream 1/2 cup softened butter with 1 cup granulated sugar until fluffy. Beat in the egg and 2 tsp vanilla extract.
  5. Mix in 1 1/2 cups all-purpose flour, 1/2 tsp baking soda, 1/4 tsp baking powder, and 1/4 tsp salt until a soft dough forms.
  6. Scoop 2–3 tablespoons of dough per cookie, flatten slightly, and press gently onto each pineapple ring.
  7. Bake for 12–15 minutes or until edges are lightly golden.
  8. Cool cookies on the baking sheet for 8–10 minutes to allow caramel to set.
  9. Carefully flip each cookie over so the pineapple ring is on top.

Notes

  • Ensure pineapple rings are well drained to prevent caramel from leaking.
  • Lightly greasing parchment is essential to prevent sticking.
  • Dough can be made ahead and chilled for up to 24 hours.
  • To make smaller cookies, use half pineapple rings and reduce baking time.
  • Chopped nuts or shredded coconut can be added for extra texture.

Nutrition

Find it online: https://savorymomskitchen.com/pineapple-upside-down-sugar-cookies/