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Sweet Pineapple Upside Down Sugar Cookies Recipe

Sweet Pineapple Upside Down Sugar Cookies


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4.9 from 37 reviews

  • Total Time: 45 minutes
  • Yield: 13 1x

Description

Spiced pineapple upside down sugar cookies blend tropical sweetness with classic bakery charm. Golden caramelized edges and rich buttery notes invite bakers to savor each delightful bite.


Ingredients

Scale
  • 1 cup (226 g/8 oz) butter, room temperature
  • 1 ½ cups (300 g/10.5 oz) granulated sugar
  • 2 eggs
  • 1 cup (220 g/7.75 oz) light brown sugar, packed
  • 3 cups (375 g/13.25 oz) all-purpose flour
  • 13 canned pineapple slices
  • 13 maraschino cherries
  • ½ cup (120 g/4.25 oz) sour cream
  • ½ cup (113 g/4 oz) butter, melted
  • 2 tsps (10 mL) vanilla extract
  • 1 tsp baking powder
  • 1 tsp cornstarch
  • ½ tsp salt

Instructions

  1. Oven Preparation: Preheat oven to 350°F (175°C) and position mini round cake pan for the pastry.
  2. Butter Mixture: Cream softened butter and granulated sugar until light and fluffy, then blend in eggs, vanilla extract, and sour cream until thoroughly combined.
  3. Dry Ingredient Integration: Whisk flour, baking powder, cornstarch, and salt, then gently fold into the wet ingredients to create a smooth cookie dough.
  4. Caramel Foundation: Whisk melted butter with brown sugar, then evenly distribute across the bottom of each mini cake pan cavity.
  5. Fruit Placement: Arrange pineapple slices over the caramel base, positioning a maraschino cherry at the center of each slice.
  6. Dough Application: Portion cookie dough over the pineapple arrangement, smoothing with an offset spatula to create a uniform surface.
  7. Baking Process: Bake for 25 minutes, monitoring for golden-brown edges and bubbling caramel.
  8. Cooling and Serving: Rest cookies in the pan for 10 minutes, then carefully invert onto wax paper, adjusting any displaced fruit. Allow to cool completely before serving.
  9. Storage: Preserve in an airtight container, consuming within 2-3 days for optimal taste and texture.

Notes

  • Caramelize with Care: Evenly spread the brown sugar mixture to create a perfect sticky base that ensures each cookie has a consistent, rich caramel flavor.
  • Precise Pineapple Placement: Position pineapple slices and cherries carefully before adding cookie dough to guarantee a beautiful, professional-looking presentation.
  • Cooling Technique: Let cookies rest in the pan for 10 minutes after baking to help them set and prevent breaking during the delicate inverting process.
  • Storage Smart: Keep cookies in an airtight container to maintain moisture and freshness, consuming within 2-3 days for the best taste and texture.
  • Prep Time: 20 minutes
  • Cook Time: 25 minutes
  • Category: Desserts, Snacks
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 13
  • Calories: 267
  • Sugar: 18 g
  • Sodium: 95 mg
  • Fat: 12 g
  • Saturated Fat: 7 g
  • Unsaturated Fat: 3 g
  • Trans Fat: 0 g
  • Carbohydrates: 38 g
  • Fiber: 0.5 g
  • Protein: 2 g
  • Cholesterol: 34 mg