Dessert

Pineapple Upside Down Sugar Cookies Recipe

ByLana Polati March 28, 2026March 28, 2026

Introduction

Pineapple Upside Down Sugar Cookies are soft, buttery sugar cookies topped with caramelized pineapple rings and sweet cherry centers. This fun twist on the classic cake brings tropical flavor into an easy, handheld dessert perfect for parties or everyday treats.

The image shows small round pineapple tarts arranged on a white surface with a white marbled texture. Each tart has a golden yellow pineapple slice on the top with a slightly glossy texture, and a dollop of bright red jam sits in the center of the pineapple slice, adding a shiny contrast. The base of the tarts is a light golden-brown color with a crumbly texture visible at the edges. The tarts are sprinkled lightly with granulated sugar that gives a sparkling effect. The focus is close, making the details of the jam and fruit texture clear and inviting. 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 ½ cups all-purpose flour
1 teaspoon baking soda
½ teaspoon salt
1 can pineapple rings, well drained
Maraschino cherries (optional, for centers)
2–3 tablespoons granulated sugar (for sprinkling)

Instructions

Step 1: Preheat your oven to 350°F (180°C) and line baking sheets with parchment paper.
Step 2: In a large bowl, cream the softened butter and sugar together for 2–3 minutes until light and fluffy.
Step 3: Add the egg and vanilla extract to the butter mixture and beat until fully combined.
Step 4: In a separate bowl, whisk together the flour, baking soda, and salt.
Step 5: Gradually mix the dry ingredients into the wet ingredients until a soft dough forms.
Step 6: Scoop about 2 tablespoons of dough per cookie onto the prepared baking sheets, spacing them about 2 inches apart.
Step 7: Gently press a well-drained pineapple ring into each dough mound. If using, place a maraschino cherry in the center of each pineapple ring.
Step 8: Sprinkle 2 to 3 tablespoons of granulated sugar over the pineapple rings to help caramelize during baking.
Step 9: Bake for 11–13 minutes, or until the edges are golden and the centers are set.
Step 10: Allow the cookies to cool on the baking sheet for 5 minutes, then transfer them to a wire rack to cool completely.

Tips & Variations

Pat pineapple rings dry with paper towels before using to prevent excess moisture in the dough.
For extra caramel flavor, substitute ¼ cup of granulated sugar in the dough with brown sugar.
Fresh pineapple can be used if sliced thin and dried well to avoid sogginess.
Dough can be made ahead and refrigerated for up to 24 hours before baking.

Storage

Store the cookies in an airtight container at room temperature for up to 2 days or refrigerate for up to 5 days. To reheat, warm cookies gently in a low oven or microwave for a few seconds to revive softness.

How to Serve

The image shows several small round treats stacked in a pile on a white plate, each treat having three visible layers: the bottom is a golden yellow cookie with a sugary texture, the middle layer is a red jam spread thickly, and the top layer is a bright yellow pineapple ring with a small dollop of the same red jam in the center. The pineapple rings have a slightly translucent look with a glossy surface, and some granulated sugar sprinkles can be seen on the top layer, adding texture. The setting is on a white marbled surface, and a few loose crumbs are scattered around the plate. The 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, you can use fresh pineapple rings if they are sliced thin and thoroughly dried to prevent excess moisture in the cookies.

How do I keep the pineapple from making the cookies soggy?

Make sure to drain and pat dry the pineapple rings well before pressing them into the dough. This helps reduce moisture and keeps the cookies soft without becoming soggy.