Description
These Pineapple Upside Down Sugar Cookies combine the nostalgic flavors of a classic cake into a delightful, portable treat. With a soft, chewy cookie base topped with caramelized pineapple and cherries, they’re sure to impress at any gathering!
Ingredients
- Canned Pineapple Rings
- Brown Sugar
- Unsalted Butter
- Maraschino Cherries
- Non-Alcoholic Rum Extract (Optional)
- All-Purpose Flour
- Granulated Sugar
- Large Egg
- Vanilla Extract
- Baking Powder
- Salt
- Almond Extract (Optional)
Instructions
- Prepare Your Topping Station: Line a large baking sheet with parchment paper or a silicone baking mat. In a small microwave-safe bowl, melt 3 tablespoons of unsalted butter. Stir in 1/4 cup of light brown sugar and, if using, 1/4 teaspoon of non-alcoholic rum extract until well combined.
- Arrange the Pineapple: Take your well-drained and patted-dry pineapple rings and arrange them evenly spaced on your prepared baking sheet. Spoon about 1/2 teaspoon of the melted brown sugar mixture into the center of each pineapple ring, spreading it slightly. Place a halved maraschino cherry in the center of each ring.
- Cream Butter and Sugar: In a large mixing bowl, cream together 1 cup of softened unsalted butter and 1 cup of granulated sugar on medium-high speed until light and fluffy, about 2-3 minutes.
- Add Wet Ingredients: Beat in 1 large room temperature egg, 1 teaspoon of vanilla extract, and if using, 1/4 teaspoon of almond extract until well combined.
- Combine Dry Ingredients: In a separate medium bowl, whisk together 2 3/4 cups of all-purpose flour, 1 teaspoon of baking powder, and 1/2 teaspoon of salt.
- Gradually Add Dry to Wet: With the mixer on low speed, gradually add the dry ingredients to the wet ingredients, mixing until just combined.
- Chill the Dough (Optional but Recommended): If your dough feels too soft to handle, flatten it into a disc, wrap it tightly in plastic wrap, and refrigerate for 30 minutes to an hour.
- Roll and Cut Cookies: Lightly flour your work surface and a rolling pin. Roll out half of the chilled dough to about 1/4-inch thickness and cut out circles of dough.
- Assemble the Cookies: Place each dough circle directly on top of one of the pineapple rings and cherries on your baking sheet. Press down lightly around the edges to seal the dough to the pineapple.
- Bake: Preheat your oven to 375°F (190°C). Bake the cookies for 10-12 minutes, or until the edges are lightly golden.
- The Critical Flip: Immediately place a wire cooling rack directly on top of the cookies. In one swift motion, carefully flip the entire baking sheet and cooling rack together so the cookies are now upside down on the rack.
- Cool Completely: Let the cookies cool completely on the wire rack.
- Prep Time: 30 mins
- Cook Time: 12 mins
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 150
- Sugar: 10 g
- Sodium: 80 mg
- Fat: 6 g
- Saturated Fat: 4 g
- Unsaturated Fat: 1 g
- Trans Fat: 0 g
- Carbohydrates: 22 g
- Fiber: 0 g
- Protein: 1 g
- Cholesterol: 20 mg
Keywords: Aim for small, 2-inch diameter canned pineapple rings for best results. Always drain and pat the pineapple dry to prevent a watery topping. Chilling the dough makes it easier to handle, and flipping the cookies immediately after baking is crucial for a successful upside-down effect.