Pineapple Upside Down Sugar Cookies Recipe
Delight in these Pineapple Upside Down Sugar Cookies, a creative twist on the classic pineapple upside-down cake. Featuring soft sugar cookie dough baked atop a caramelized brown sugar and butter base, each cookie is topped with a juicy pineapple slice and a bright maraschino cherry. Perfect for a sweet treat that combines tropical flavors with a buttery, tender cookie texture.
- Prep Time: 15 minutes
- Cook Time: 25 minutes
- Total Time: 40 minutes
- Yield: 13 cookies 1x
- Category: Dessert
- Method: Baking
- Cuisine: American
Ingredients
Scale
Cookie Dough
- 1 cup butter (room temperature)
- 1 1/2 cups granulated sugar
- 2 eggs
- 2 tsp vanilla extract
- 1/2 cup sour cream
- 3 cups all-purpose flour
- 1 tsp baking powder
- 1 tsp cornstarch
- 1/2 tsp salt
Topping
- 13 canned pineapple slices
- 13 maraschino cherries
- 1/2 cup butter (melted)
- 1 cup light brown sugar (packed)
Instructions
- Preheat Oven: Preheat your oven to 350 degrees Fahrenheit. Prepare a USA pan mini round cake pan for baking.
- Mix Butter and Sugar: In a large mixing bowl, cream together the room temperature butter and granulated sugar until the mixture is light and fluffy, about 2-3 minutes.
- Add Wet Ingredients: Incorporate the eggs, vanilla extract, and sour cream into the butter-sugar mixture. Mix until all ingredients are fully combined and smooth.
- Add Dry Ingredients: Gradually add the all-purpose flour, baking powder, cornstarch, and salt. Mix just until the cookie dough comes together. Avoid overmixing to keep cookies tender.
- Prepare Brown Sugar Mixture: In a separate bowl, combine the melted butter and packed light brown sugar until well blended.
- Assemble Cookie Bases: Spoon about 1 tablespoon of the brown sugar mixture evenly into the bottom of each cavity of the mini round cake pan. Spread to cover the base evenly.
- Add Pineapple Slice and Cherry: Place one pineapple slice atop the brown sugar in each cavity, then center a maraschino cherry on top of each pineapple slice.
- Top with Cookie Dough: Using a 3 tablespoon cookie scoop, place a scoop of cookie dough over each pineapple and cherry arrangement. Flatten gently with an offset spatula to cover the top evenly.
- Bake: Place the pan into the preheated oven and bake for about 25 minutes, or until the cookie edges turn golden brown and the brown sugar mixture is bubbling up the sides.
- Cool and Release: Allow the cookies to cool in the pan for 10 minutes. Then carefully invert the pan onto a wax paper-lined surface to release the cookies. Be cautious as the brown sugar may run.
- Final Cooling and Storage: Let the cookies cool completely before serving. Store them in an airtight container. These cookies are best enjoyed within 2 to 3 days for optimal freshness.
Notes
- Use wax paper when turning out the cookies to catch sticky, melted brown sugar for easy cleanup.
- If the pineapple slices stick to the pan when flipping, reposition them carefully back onto the tops of the cookies.
- Room temperature butter helps achieve a light, fluffy cookie dough texture for tender cookies.
- Do not overmix the dough once dry ingredients are added to avoid tough cookies.
- These cookies are best eaten within a few days as the pineapple topping is fresh and juicy.
Keywords: Pineapple upside down cookies, sugar cookies, pineapple cookies, holiday cookies, fruit topped cookies, caramelized brown sugar cookies
