Ingredients and what they do
- 1 cup unsalted butter, softened
Provides richness and tenderness and creams easily with sugar, forming the base structure of the sugar cookie. - 1 cup granulated sugar
Sweetens and aerates the butter when creamed, helping create a light, soft cookie crumb. - 1 large egg
Binds the dough and adds moisture and structure, as in most sugar cookie formulas. - 1 teaspoon vanilla extract
Adds warm, sweet aroma that complements the tropical fruit and coconut. - 2 1/2 cups all-purpose flour
Provides structure. Similar pineapple upside cookie recipes use about 2 1/2–3 cups flour for a sturdy base that supports the fruit topping. - 1/2 teaspoon baking powder
Gives gentle lift without too much spread, keeping the cookies thick enough to hold the pineapple. - 1/4 teaspoon salt
Balances sweetness and enhances flavor. - 1 cup sweetened shredded coconut
Adds chew and coconut flavor, echoing coconut–pineapple and piña colada cookie styles. - 12 pineapple rings, well-drained
Provide tangy-sweet, juicy topping and the signature upside-down cake look. Recipes stress draining well and sometimes patting dry to avoid excess moisture. - 12 maraschino cherries, drained and patted dry
Nestled in the center of each ring for color and classic pineapple upside-down presentation.
Step-by-step instructions
Prepare the oven and pan
Preheat your oven to 350°F (175°C). Line a large baking sheet with parchment paper. Baking at 350°F on parchment is standard for pineapple upside and sugar cookie hybrids to prevent sticking and encourage even browning.
Make the sugar cookie dough
In a large mixing bowl, cream together the softened butter and granulated sugar with a hand mixer or stand mixer on medium speed for 2–3 minutes, until pale and fluffy. This creaming step, also used in other pineapple upside sugar cookie recipes, incorporates air for a lighter cookie texture.
Add the egg and vanilla extract. Continue mixing on medium speed until the mixture is smooth and creamy, scraping the bowl as needed.
In a separate bowl, whisk together the all-purpose flour, baking powder, and salt until evenly combined. Whisking dry ingredients first ensures the leavening is distributed, a standard step in sugar cookie recipes.
Gradually add the dry mixture to the butter mixture, mixing on low speed just until a soft, pliable dough forms. Avoid overmixing, which can toughen sugar cookies, as many recipes caution.
Fold in the sweetened shredded coconut until evenly distributed throughout the dough.
Shape the cookie bases
Scoop about 2 tablespoons of dough and roll into a ball. Flatten each ball into a round disk using your hands or the bottom of a glass. Place the disks on the prepared baking sheet, spacing them a few inches apart to allow for some spread. Shaping into thick disks mirrors how many pineapple upside-down sugar cookie recipes prep their bases.
Add pineapple and cherries
Gently press a well-drained pineapple ring onto each dough disk, centering it so the ring sits neatly on top and presses slightly into the dough. Well-drained slices are essential to prevent excess moisture from seeping into the cookies, as noted in multiple recipes.
Place a drained and patted-dry maraschino cherry in the center hole of each pineapple ring, pressing lightly to adhere.
At this point, some upside-down cookie recipes add a small sprinkle of brown sugar or a dab of melted butter around the fruit for extra caramelization; you can do this for a more cake-like finish if desired.
Bake
Bake at 350°F (175°C) for about 12–15 minutes, or until the cookie edges are lightly golden and the bottoms are set. Sugar cookie–based pineapple upside cookies generally bake within this range, with edges just turning color and centers set but still soft.
Let the cookies cool on the baking sheet for about 5–10 minutes to firm up. Then carefully transfer them to a wire rack to cool completely. Many pineapple upside cookie recipes emphasize cooling so the fruit-topped cookies don’t break when moved.