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A close-up of a Pineapple Upside Sugar Cookie topped with a pineapple slice and a maraschino cherry.

Pineapple Upside Sugar Cookies

Make these Pineapple Upside Sugar Cookies using a muffin tin for a fun twist on a classic dessert. These cookies feature a caramel base, a slice of pineapple, and a cherry center, all topped with soft cookie dough.
Prep Time 15 minutes
Cook Time 14 minutes
Total Time 29 minutes
Servings: 12 cookies
Course: Dessert
Cuisine: American
Calories: 150

Ingredients
  

For the Caramel Base and Fruit
  • 2 tablespoons Unsalted Butter For melting
  • 1/4 cup Brown Sugar Light or Dark
  • 1 ring or portion Canned Pineapple Well-drained
  • 1 piece Maraschino Cherries Halved
For the Cookie Dough
  • 1/2 cup Unsalted Butter Softened
  • 3/4 cup Granulated Sugar
  • 1 Egg At room temperature
  • 1 teaspoon Vanilla Extract
  • 1 1/2 cups All-Purpose Flour
  • 1 teaspoon Baking Powder
  • 1/4 teaspoon Salt

Equipment

  • 12-cup standard muffin tin or two 24-cup mini muffin tins
  • Electric mixer
  • Small microwave-safe bowl
  • Medium bowl
  • Wire cooling rack

Method
 

  1. Preheat your oven to 375°F (190°C). Grease a 12-cup standard muffin tin or two 24-cup mini muffin tins.
  2. If using pineapple rings, drain them well and pat them dry. Halve your maraschino cherries. Set the fruit aside.
  3. In a small, microwave-safe bowl, melt 2 tablespoons of unsalted butter. Stir in 1/4 cup of brown sugar until combined. Spoon about 1/2 teaspoon of this mixture into the bottom of each prepared muffin cup.
  4. Place one piece of prepared pineapple on top of the brown sugar mixture in each muffin cup. Place a cherry half in the center of each pineapple piece.
  5. In a large mixing bowl, cream together the remaining 1/2 cup of softened unsalted butter and 3/4 cup of granulated sugar until the mixture is light and pale yellow.
  6. Beat in the egg and vanilla extract until fully mixed. Scrape down the sides of the bowl.
  7. In a separate medium bowl, whisk together the all-purpose flour, baking powder, and salt.
  8. Gradually add the dry ingredient mixture to the wet ingredients, mixing on low speed until just combined.
  9. Use a small cookie scoop or two spoons to place about 1 tablespoon of cookie dough on top of the pineapple and cherry in each muffin cup.
  10. Bake for 10-14 minutes for standard tins, or 8-10 minutes for mini tins.
  11. Remove the muffin tin from the oven and let the cookies cool in the tin for 5-7 minutes. Place a wire cooling rack over the top of the muffin tin, and carefully invert the entire tin onto the rack.

Nutrition

Calories: 150kcalCarbohydrates: 22gProtein: 1gFat: 6gSaturated Fat: 4gCholesterol: 20mgSodium: 50mgSugar: 10g

Notes

This recipe uses the muffin tin method to create a soft, slightly chewy cookie that holds the fruit topping in place. The caramel layer forms nicely on the bottom, which becomes the top after flipping.

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