Description

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 pineapple upside down cake delivers tropical flavor in an easy-to-make, handheld dessert perfect for parties, holidays, or everyday baking.

Ingredients

Scale

For the Cookie Base

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

For the Topping

1 can pineapple rings, well drained
Maraschino cherries (optional, for centers)
2–3 tablespoons granulated sugar (for sprinkling)

Instructions

Preheat Oven: Preheat your oven to 350°F (180°C) and line baking sheets with parchment paper to prevent sticking.
Cream Butter and Sugar: In a large bowl, cream the softened butter and granulated sugar together for 2–3 minutes until the mixture is light and fluffy, creating a smooth base for the cookie dough.
Add Egg and Vanilla: Beat in the egg and vanilla extract until fully combined, which helps bind the dough and enhance flavor.
Mix Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt to evenly distribute the leavening and seasoning.
Combine Wet and Dry Ingredients: Gradually mix the dry ingredients into the wet ingredients until a soft dough forms, careful not to overmix to keep cookies tender.
Portion Dough onto Sheets: Scoop about 2 tablespoons of dough per cookie onto the prepared baking sheets, spacing them about 2 inches apart to allow spreading.
Add Pineapple and Cherry Topping: Gently press a well-drained pineapple ring into each dough mound and place a maraschino cherry in the center if using, adding the signature look and flavor.
Sprinkle Sugar: Sprinkle 2–3 tablespoons of granulated sugar evenly over the pineapple rings to promote caramelization during baking.
Bake Cookies: Bake in the preheated oven for 11–13 minutes until the edges are golden brown and the centers are set, ensuring the cookies are cooked through but still soft.
Cool Cookies: Allow the cookies to cool on the baking sheet for 5 minutes after removal from the oven, then transfer them to a wire rack to cool completely before serving.

Notes

Pat pineapple rings dry thoroughly to prevent excess moisture from making the dough soggy.
For extra caramel flavor, replace ¼ cup of the granulated sugar in the dough with brown sugar.
Store cookies in an airtight container at room temperature for up to 2 days, or refrigerate them for up to 5 days to maintain freshness.
Dough can be prepared ahead of time and refrigerated for up to 24 hours before baking.
If using fresh pineapple instead of canned, slice thinly and dry well to avoid adding too much moisture.

Prep Time: 15 minutes
Cook Time: 13 minutes
Category: Dessert
Method: Baking
Cuisine: American

Keywords: pineapple upside down sugar cookies, pineapple cookies, caramelized pineapple dessert, soft sugar cookies, tropical cookies, holiday cookies, party desserts