Classic Pineapple Upside-Down Sugar Cookies
A nostalgic dessert transformed into a bite-sized treat
Classic Pineapple Upside-Down Sugar Cookies take everything people love about the traditional pineapple upside-down cake and turn it into charming, individual cookies. They feature a glossy caramelized pineapple topping with a bright cherry center, baked over a soft, buttery sugar cookie base. These cookies are eye-catching, tender, and full of tropical sweetness—perfect for holidays, bake sales, or anytime you want something fun and familiar with a twist.
This recipe is simple, approachable, and designed to give you bakery-style results at home.
What Makes These Cookies Special
- Mini version of a classic dessert – All the flavor of pineapple upside-down cake in cookie form
- Beautiful presentation – Naturally decorative, no icing required
- Soft and buttery texture – Thanks to the sugar cookie base
- Perfectly balanced flavor – Sweet caramel, tangy pineapple, and rich butter
Ingredients You’ll Need
For the Pineapple Topping
- ¼ cup unsalted butter, melted
- ½ cup brown sugar, packed
- Pineapple rings or tidbits (well drained and patted dry)
- Maraschino cherries, halved
For the Sugar Cookie Dough
- ¾ cup unsalted butter, softened
- ¾ cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 2 cups all-purpose flour
- ½ teaspoon baking powder
- ¼ teaspoon salt
Step-by-Step Method
Step 1: Prepare the Baking Pan
Preheat your oven to 350°F (175°C). Lightly grease a muffin tin or line it with parchment paper circles. Using a muffin tin helps the cookies hold the pineapple topping neatly and creates the classic “upside-down” look.
Step 2: Create the Pineapple Base
In a small bowl, mix the melted butter and brown sugar until smooth. Spoon about 1 teaspoon of this mixture into the bottom of each muffin cup.
Place a small piece of pineapple on top of the sugar mixture. Add a cherry half in the center of the pineapple. Press gently so it sits flat.
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