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Delicious Upside Down Cake Pineapple Sugar Cookies topped with caramelized pineapple and cherries.

Upside Down Cake Pineapple Sugar Cookies

A delightful twist on the classic pineapple upside-down cake transformed into fun, bite-sized cookies with a sweet and buttery flavor.
Servings 24 cookies
Prep Time 20 minutes
Cook Time 12 minutes
Total Time 32 minutes

Ingredients

For the Cookie Base

  • 1 cup Butter, softened
  • 1 cup Granulated sugar
  • 1/2 cup Brown sugar Dark brown sugar preferred for a deeper flavor
  • 1 large Egg
  • 1 teaspoon Vanilla extract
  • 2 cups All-purpose flour
  • 1 teaspoon Baking powder
  • 1/4 teaspoon Salt

For the Topping

  • 1 can Pineapple rings Cut into small pieces and pat dry
  • 24 pieces Maraschino cherries Optional, for decoration
  • 1/2 cup Pineapple juice From the canned pineapple, optional for extra flavor
  • 1-2 teaspoons Brown sugar For the topping spots on the baking sheet

Instructions

Preparation

  • Heat the oven to 350°F and line baking sheets with parchment paper.
  • On the parchment, sprinkle small circles of brown sugar (1-2 teaspoons) and top with a piece of pineapple and a cherry half if using.
  • Cream together softened butter and granulated sugar until fluffy. Beat in the egg and vanilla, then stir in flour, baking powder, and salt until a soft dough forms.
  • Scoop dough balls and gently press over the pineapple topping. Do not flatten completely.

Baking

  • Bake for 10-12 minutes until edges are set and barely golden.
  • Let the cookies rest for 2-3 minutes, then carefully flip them using a thin spatula.

Notes

Pat the pineapple dry to avoid a slippery topping. Chill the dough if your kitchen is warm to maintain cookie shape.

Nutrition

Serving: 1gCalories: 150kcalCarbohydrates: 18gProtein: 1gFat: 8gSaturated Fat: 5gSodium: 50mgSugar: 10g
Author: Emma Novich
Calories: 150kcal
Course: Dessert, Snack
Cuisine: American, Baked
Keyword: Cookie Recipe, Pineapple Cookies, Pineapple Dessert, Sugar Cookies, Upside Down Cookies