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–+ servings
Pineapple Upside Down Sugar Cookies

Pineapple Upside Down Sugar Cookies That Spark Joy

Delight in these Pineapple Upside Down Sugar Cookies, a whimsical twist on the classic dessert with a chewy texture and caramelized topping.
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Prep Time 20 minutes
Cook Time 12 minutes
Cooling Time 5 minutes
Total Time 37 minutes
Servings: 12 cookies
Course: Desserts
Cuisine: American
Calories: 150
Ingredients Equipment Method Nutrition Notes

Ingredients
  

For the Cookie Base
  • 1 3/4 cups all-purpose flour whole wheat flour optional
  • 1/2 cup granulated sugar coconut sugar optional
  • 1/2 cup brown sugar can substitute with granulated sugar and molasses
  • 1/2 cup unsalted butter use vegan butter for dairy-free option
  • 1 large egg flax egg can be a substitute
  • 1 teaspoon baking powder no substitutions typically required
  • 1 pinch salt reducing salt can affect flavor
For the Topping
  • 1 can canned pineapple rings fresh pineapple can be used
  • 1/2 cup brown sugar for caramelization
  • 2 tablespoons unsalted butter

Equipment

  • Mixing bowl
  • Electric mixer
  • Baking Sheet
  • Parchment Paper
  • Saucepan

Method
 

Step‑by‑Step Instructions
  1. Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
  2. Cream together the unsalted butter, granulated sugar, and brown sugar until light and fluffy (3-5 minutes).
  3. Beat in one large egg until fully incorporated (1-2 minutes).
  4. Whisk together all-purpose flour, baking powder, and salt in a separate bowl, then mix into wet ingredients until a dough forms.
  5. In a saucepan, combine brown sugar and butter until melted and bubbly, then spread in the baking sheet and add pineapple rings.
  6. Dollop cookie dough over the topping and sprinkle maraschino cherries in the center of each pineapple ring.
  7. Bake for 10-12 minutes until edges are lightly golden and center is set.
  8. Cool for 5 minutes in the pan before inverting onto a serving plate.

Nutrition

Serving: 1cookieCalories: 150kcalCarbohydrates: 20gProtein: 2gFat: 7gSaturated Fat: 4gPolyunsaturated Fat: 1gMonounsaturated Fat: 2gCholesterol: 30mgSodium: 75mgPotassium: 60mgSugar: 10gVitamin A: 200IUVitamin C: 1mgCalcium: 20mgIron: 0.5mg

Notes

For best results, keep ingredients at room temperature and do not overmix the dough.

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