Pineapple Upside Down Sugar Cookies

Looking for a dessert that blends retro charm with modern convenience?
These Pineapple Upside Down Sugar Cookies are inspired by the classic pineapple upside down cake, but reimagined in a fun, handheld cookie form.
Each cookie is soft, buttery, and lightly crisp around the edges, topped with a juicy pineapple ring that caramelizes beautifully in the oven.

Upside down cakes gained popularity in the 1920s with the rise of canned pineapple, and this recipe pays homage to that nostalgic favorite—without the fuss of a full cake.
Perfect for summer gatherings, holiday cookie trays, bake sales, or when you want something cheerful and different.

Ingredients

1 cup unsalted butter, softened – creates a rich, tender cookie base
1 cup granulated sugar – sweetens and helps produce a light texture
1 large egg – binds the dough and adds moisture
1 teaspoon vanilla extract – enhances flavor and warmth
2 cups all-purpose flour – provides structure
1 teaspoon baking soda – helps the cookies rise slightly
1/2 teaspoon salt – balances sweetness
10–12 canned pineapple rings, well-drained and patted dry
Additional granulated sugar, for sprinkling on top

Instructions

Preheat the oven to 350°F (180°C).
Line two baking sheets with parchment paper or silicone baking mats.
In a large mixing bowl, cream together the butter and sugar until light and fluffy, about 2–3 minutes using an electric mixer.
Add the egg and vanilla extract, mixing until smooth and fully incorporated.
In a separate bowl, whisk together flour, baking soda, and salt.
Gradually add the dry ingredients to the wet ingredients, mixing just until combined. Do not overmix.
Scoop about 2 tablespoons of dough per cookie and place onto prepared baking sheets, spacing cookies about 2 inches apart.
Gently press a pineapple ring onto each dough mound, flattening slightly.
If needed, cut the rings in half to better fit the cookies.
Sprinkle a small amount of sugar over the pineapple tops to encourage caramelization and add sparkle.
Bake for 11–13 minutes, or until the edges are lightly golden and the centers are set.
Allow cookies to cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.

✨ Tips & Variations

Add a maraschino cherry in the center of each pineapple ring for a classic look.
For extra flavor, brush pineapple rings lightly with melted butter before placing on dough.
Store cookies in an airtight container at room temperature for up to 3 days.

Sweet, nostalgic, and irresistibly fun — these Pineapple Upside Down Sugar Cookies are guaranteed to brighten any dessert table. Enjoy every sunny bite!