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Pineapple Whoopie Pies with Cream Cheese Pineapple Filling Recipe

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Pineapple Whoopie Pies offer a delightful twist on the classic treat, featuring soft, cake-like cookies paired with a creamy pineapple cheesecake filling. Perfect for dessert lovers seeking a nostalgic yet flavorful indulgence, these whoopie pies bring together tropical pineapple and rich cream cheese for an irresistible bite.

Ingredients

Cookie Ingredients

  • 1 box pineapple cake mix (can use yellow if preferred)
  • ½ cup oil
  • ½ cup pineapple juice
  • 3 large eggs

Filling Ingredients

  • 1 stick (4 oz) butter, softened
  • 8 oz cream cheese, softened
  • 1 teaspoon vanilla extract
  • 1 cup powdered sugar, plus extra for dusting
  • ½ cup crushed pineapple, drained well

Instructions

  1. Preheat the Oven: Set your oven to 350 degrees Fahrenheit to ensure proper baking temperature for the cookies.
  2. Prepare Baking Sheets: Line cookie sheets with parchment paper to prevent sticking and ease cleanup.
  3. Mix Cookie Batter: In a large bowl, combine the pineapple cake mix, oil, pineapple juice, and eggs using a mixer until the batter is smooth and fully integrated.
  4. Portion Batter: Drop heaping tablespoons of the batter onto the prepared cookie sheets, spacing them about 3 inches apart to allow for spreading during baking.
  5. Bake Cookies: Place cookie sheets on the center rack of the oven and bake for approximately 10 minutes or until the edges are browned.
  6. Cool Cookies: Remove the cookies from the oven and allow them to cool in the pan placed on a baking rack to prevent sogginess.
  7. Prepare Filling: In a mixing bowl, cream the softened butter, cream cheese, and vanilla extract until the mixture is light and fluffy.
  8. Add Sugar and Pineapple: Incorporate the powdered sugar into the cream mixture and blend well before gently folding in the well-drained crushed pineapple.
  9. Assemble Whoopie Pies: Spread a generous amount of the pineapple cream filling onto half of the cooled cookies, then sandwich them with the remaining cookies.
  10. Final Touch: Dust the tops of the assembled whoopie pies lightly with powdered sugar for an elegant finish.

Notes

  • Ensure the crushed pineapple is well-drained to avoid soggy filling.
  • Allow the cookies to cool completely before assembling to prevent the filling from melting.
  • You can substitute yellow cake mix if pineapple flavor is not preferred for the cookies.
  • For a firmer filling, chill the assembled whoopie pies before serving.