Pineapple Upside Down Cookies

User Reviews

5.0

3 reviews
Excellent
  • Prep Time

    15 mins

  • Cook Time

    15 mins

  • Total Time

    40 mins

  • Servings

    18 cookies

  • Calories

    245 kcal

  • Course

    Dessert

  • Cuisine

    American

Pineapple Upside Down Cookies

Get all the tropical sweetness of pineapple upside-down cake in a super soft cookie featuring caramelized pineapple and juicy cherries.

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Ingredients

Servings
  • 2 (20-ounce can) pineapple rings drained
  • 9 Maraschino cherries halved
  • 1/2 cup brown sugar
  • 1 cup unsalted butter softened
  • 3/4 cup brown sugar
  • 1/2 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 3 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
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Instructions

  1. Preheat your oven to 400°F (204°C). Line two baking sheets with parchment paper or silicone baking mats.
  2. Drain the juice from 2 (20-ounce can) pineapple rings. Use paper towels or a clean dish towel to pat them dry. Place the rings, evenly spaced, on the prepared baking sheets, about 9 per pan. Place a halved maraschino cherry in the center. Sprinkle each pineapple ring with a small spoonful of brown sugar, about 1 1/2 teaspoons per ring.
  3. Bake in the oven for about 10 minutes, until the brown sugar has candied onto the pineapple. Remove trays from oven and let cool while you make the cookie dough.
  4. In a large mixing bowl use a hand mixer to beat 1 cup unsalted butter (softened), 3/4 cup brown sugar, and 1/2 cup granulated sugar until smooth and creamy, about 3 minutes. It should become pale, fluffy, and visibly lighter in color.
  5. Add 2 large eggs, and 1 teaspoon vanilla extractBeat on low speed until just combined, about 30 seconds.
  6. Add 3 cups all-purpose flour, 1 teaspoon baking powder, 1 teaspoon baking soda, and 1/2 teaspoon salt. Mix until just combined.
  7. Take about 2 tablespoons of the dough and form a ball, and set it on top of each candied pineapple ring. Gently press the dough to flatten it just enough to adhere it to the ring.
  8. Return the pans to the oven to bake the cookies for 12 to 14 minutes, until the tops of the cookies are golden brown.
  9. Allow the cookies to cool on the baking sheets for 15 minutes before serving warm. Alternatively, transfer them to a wire rack to cool completely.

Notes

  • The fruit means these cookies require refrigeration. Store these cookies in an airtight container or plastic bag in the refrigerator for up to 5 days. 

Nutrition Information

Show Details
Serving 1cookie Calories 245kcal (12%) Carbohydrates 37g (12%) Protein 3g (6%) Fat 10g (15%) Saturated Fat 6g (30%) Polyunsaturated Fat 1g Monounsaturated Fat 3g Trans Fat 0.4g Cholesterol 43mg (14%) Sodium 198mg (8%) Potassium 74mg (2%) Fiber 1g (4%) Sugar 22g (44%) Vitamin A 316IU (6%) Vitamin C 0.3mg (0%) Calcium 34mg (3%) Iron 1mg (6%)

Nutrition Facts

Serving: 18cookies

Amount Per Serving

Calories 245 kcal

% Daily Value*

Serving 1cookie
Calories 245kcal 12%
Carbohydrates 37g 12%
Protein 3g 6%
Fat 10g 15%
Saturated Fat 6g 30%
Polyunsaturated Fat 1g 6%
Monounsaturated Fat 3g 15%
Trans Fat 0.4g 20%
Cholesterol 43mg 14%
Sodium 198mg 8%
Potassium 74mg 2%
Fiber 1g 4%
Sugar 22g 44%
Vitamin A 316IU 6%
Vitamin C 0.3mg 0%
Calcium 34mg 3%
Iron 1mg 6%

* Percent Daily Values are based on a 2,000 calorie diet.

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Overall Rating

5.0

3 reviews
Excellent

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