Dessert

Irresistible Pineapple Upside Down Sugar Cookies Recipe

Byreem everly January 9, 2026January 9, 2026

Introduction

Irresistible Pineapple Upside Down Sugar Cookies offer a fun and tropical twist on the classic pineapple upside-down cake. With a buttery sugar cookie base topped with caramelized pineapple and a cherry, they make a sweet treat that’s perfect for any occasion.

The image shows close-up of small round cakes with three visible layers stacked from bottom to top: a light golden brown crumbly cake base, a glossy caramelized yellow pineapple ring with visible texture and juicy details, and a bright red cherry placed in the center on top of the pineapple. The cakes are resting on a white plate on a white marbled surface, and the focus is sharp on the nearest cake while the others blur softly in the background. photo taken with an iphone --ar 4:5 --v 7

Ingredients

1 cup unsalted butter (softened)
1 cup granulated sugar
1 large egg
1 teaspoon vanilla extract
2 1/2 cups all-purpose flour
1 teaspoon baking soda
1/2 teaspoon salt
1 can (20 oz) pineapple slices (drained)
1/4 cup brown sugar
Maraschino cherries (for garnish)

Instructions

Step 1: Preheat your oven to 350°F (175°C) and line baking sheets with parchment paper.
Step 2: In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. Beat in the egg and vanilla extract until combined.
Step 3: In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add these dry ingredients to the wet mixture, mixing until just combined.
Step 4: Cut the drained pineapple slices into smaller pieces if desired. In a small bowl, mix the brown sugar with a little pineapple juice to form a paste.
Step 5: Using a cookie scoop or tablespoon, drop cookie dough onto the prepared baking sheets, spacing each about 2 inches apart.
Step 6: Press a piece of pineapple onto the center of each cookie. Drizzle a small amount of the brown sugar mixture over the pineapple and top with a maraschino cherry.
Step 7: Bake for 12–15 minutes, until the edges are lightly golden. Let the cookies cool on the baking sheets for a few minutes before transferring to a wire rack to cool completely.
Step 8: Serve the cookies warm or at room temperature and enjoy!

Tips & Variations

Add shredded coconut to the dough for an extra tropical flavor.
Use fresh pineapple instead of canned for a fresher taste.
Sprinkle a pinch of cinnamon or nutmeg into the cookie dough to enhance the flavor complexity.

Storage

Store the cookies in an airtight container at room temperature for up to 3 days. To keep them fresh longer, refrigerate for up to a week. Reheat gently in the oven or microwave before serving for the best texture and flavor.

How to Serve

A close-up image shows four pineapple upside-down mini cakes on a white plate placed on a white marbled surface. Each small round cake has two layers: a golden brown, textured cake base with a slightly crisp, crumbly edge, topped with a glossy, caramelized pineapple slice in a yellow-orange color. At the center of the pineapple slice sits a bright, shiny red maraschino cherry, creating a vibrant contrast. The cakes are arranged closely but not touching, with a soft focus on the background cakes. photo taken with an iphone --ar 4:5 --v 7

Serve this delicious recipe with your favorite sides.

FAQs

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple works well and can give the cookies a brighter, fresher flavor. Just be sure to drain it well to avoid extra moisture in the cookies.

How do I prevent the cookies from spreading too much?

Make sure your butter is softened but not melted, and avoid over-mixing the dough. Chilling the dough briefly before baking can also help maintain the cookie shape.