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Pineapple Upside Down Cookies Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 4.6 from 143 reviews
  • Author: Jasmine
  • Prep Time: 15 minutes
  • Cook Time: 9 minutes
  • Total Time: 24 minutes
  • Yield: 12 cookies
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Description

Pineapple Upside Down Cookies are a delightful twist on the classic dessert, combining buttery, soft cookies with caramelized pineapple rings and maraschino cherries baked on the bottom of each cookie. These single-serve treats feature a rich brown sugar and butter topping that caramelizes during baking, creating a sweet, tropical flavor perfect for any occasion.

Ingredients

Units Scale

Cookie Ingredients

  • 1/2 cup Butter, softened
  • 1/2 cup Granulated Sugar (100g)
  • 1 Large Egg
  • 1 teaspoon Vanilla Extract
  • 1/2 cup Powdered Sugar (65g)
  • 1/4 cup Vegetable Oil
  • 1/2 teaspoon Baking Soda
  • 1/2 teaspoon Cream of Tartar
  • 2 cups All Purpose Flour (240g)

Pineapple Topping

  • Pineapple Rings, drained
  • Maraschino Cherries, drained
  • 6 tablespoons Butter, melted
  • 1 cup Brown Sugar (214g)

Instructions

  1. Pan Preparation: Preheat the oven to 350°F (175°C). In a small bowl, mix ½ cup melted butter with 1 cup brown sugar until well combined. Drain the pineapple rings thoroughly. Spoon about 1 tablespoon of the brown sugar and butter mixture into each well of a muffin tin. Place a pineapple ring on top of the brown sugar in each well and center a maraschino cherry within each pineapple ring. Arrange the pineapple pieces so cookies can spread without touching.
  2. Cookie Dough Preparation: In a mixing bowl, cream softened butter and granulated sugar together until the mixture is light and fluffy, scraping the bowl sides as needed. Add the egg and vanilla extract, continuing to beat for 2-3 minutes until well incorporated. Gradually add vegetable oil and powdered sugar, mixing until the batter turns pale yellow and smooth.
  3. Add Dry Ingredients: Sift together the all-purpose flour, baking soda, and cream of tartar. Gradually add these dry ingredients into the wet mixture, mixing until the dough is fully combined.
  4. Assemble Cookies: Using a size #24 cookie scoop, scoop portions of dough and press each into a flat disc approximately 3 inches in diameter. Place each flattened cookie dough disc on top of the pineapple and cherry in each muffin well. Carefully press the dough down slightly and tuck the edges into the sides of the well, sealing the edges around the topping.
  5. Bake: Bake the cookies in the preheated oven at 350°F for 8-10 minutes, until the cookie edges are lightly golden and the centers are no longer glossy.
  6. Cool and Flip: Remove the muffin tin from the oven and immediately invert the pan onto a parchment-lined baking sheet. The cookies will drop out onto the sheet, revealing the caramelized pineapple and cherry topping on top.
  7. Serve: Allow the cookies to cool completely before serving to enjoy the crisp edges and tender pineapple centers.

Notes

  • Storage: Store the cookies in an airtight container at room temperature for up to 7 days. For optimal freshness, consume within 2-3 days.
  • Freezing: Due to the high moisture content from the pineapple and cherry toppings, freezing is not recommended as the texture may become watery upon thawing.
  • Tip: Stagger the cookies’ positions in the muffin tin to avoid them spreading and touching during baking.

Nutrition

  • Serving Size: 1 cookie
  • Calories: 180 kcal
  • Sugar: 15 g
  • Sodium: 90 mg
  • Fat: 9 g
  • Saturated Fat: 4 g
  • Unsaturated Fat: 4 g
  • Trans Fat: 0 g
  • Carbohydrates: 23 g
  • Fiber: 1 g
  • Protein: 2 g
  • Cholesterol: 30 mg

Find it online: https://jmrecipes.com/pineapple-upside-down-cookies-recipe/