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Pineapple Upside Down Sugar Cookies Recipe

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Pineapple Upside Down Sugar Cookies bake soft sugar cookie dough over caramelized pineapple rings and maraschino cherries in muffin tins, then flipped for perfect handheld cake presentation. Iconic tropical dessert reimagined as chewy cookie perfection.

Ingredients

Scale
  • Sugar Cookie Dough:
  • 1 cup unsalted butter, softened
  • 1½ cups granulated sugar
  • 2 large eggs
  • 2 tsp vanilla extract
  • ½ cup sour cream
  • 3½ cups all-purpose flour
  • 1 tsp baking powder
  • 1 tsp cornstarch
  • ½ tsp salt
  • Topping:
  • 13 canned pineapple slices, drained
  • 13 maraschino cherries, drained
  • ½ cup unsalted butter, melted
  • 1 cup packed light brown sugar

Instructions

  • 1. Preheat oven to 350°F. Spray standard muffin tin generously with cooking spray.
  • 2. Make brown sugar topping: Stir melted butter and brown sugar until smooth. Spoon 1 tbsp into each muffin cup, spreading to cover bottom.
  • 3. Place one pineapple slice in each cup, pressing gently. Center a maraschino cherry in each pineapple hole.
  • 4. Cream butter and sugar 2 minutes until fluffy. Add eggs, vanilla, sour cream; mix until combined. Add flour, baking powder, cornstarch, salt; mix just until dough forms.
  • 5. Scoop 3 tbsp dough (cookie scoop #24) onto each pineapple. Gently flatten and press edges to seal. Bake 22-25 minutes until edges golden and brown sugar bubbles.
  • 6. Cool in tin 10 minutes. Run knife around edges. Invert onto parchment-lined tray. Reposition any stuck pineapple. Cool completely.

Notes

  • Sour cream creates tender chewy cookie texture.
  • Cornstarch keeps cookies soft for days.
  • Generous pan spray prevents sticking.
  • Room temperature butter essential for proper creaming.
  • Store airtight 3 days room temp, 1 week refrigerated, 2 months frozen.

Nutrition

Keywords: pineapple upside down sugar cookies, tropical cookies, pineapple cherry cookies

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