Pineapple Upside-Down Sugar Cookies
Equipment
- 1 large mixing bowl
- 1 stand mixer or hand mixer
- 2 Standard 12-cup muffin pan
- 1 Medium saucepan
- 1 Whisk
- 1 Rubber spatula
- 1 Cookie scoop 1.5-tablespoon
- 1 wire cooling rack
- 1 Cutting board
- 1 Chef's knife
- 1 pastry brush
Ingredients
- 113 gram unsalted butter softened
- 150 gram granulated sugar
- 50 gram light brown sugar packed
- 1 large egg room temperature
- 1 teaspoon vanilla extract
- 180 gram all-purpose flour
- 1/2 teaspoon baking powder
- 1/4 teaspoon baking soda
- 1/4 teaspoon fine salt
- 60 milliliter pineapple juice room temperature
- 42 gram unsalted butter for topping
- 100 gram light brown sugar for topping
- 12 maraschino cherries halved
- 1 can pineapple rings 398 ml, drained and patted dry
Instructions
- Preheat the oven to 350°F (175°C) and lightly grease two standard muffin pans.
- In a saucepan melt 42 g butter over medium heat, whisk in 100 g brown sugar, and simmer 30 seconds until glossy.
- Divide the warm brown sugar-butter mixture evenly among 24 muffin cups, about 1 teaspoon per cup.
- Cut pineapple rings into small wedges to fit muffin cups and pat very dry with paper towels.
- Place a pineapple wedge and a cherry half cut-side down into each sugared muffin cup.
- In a large bowl beat 113 g softened butter with granulated sugar and 50 g brown sugar until light and fluffy, 2 to 3 minutes.
- Beat in the egg and vanilla until smooth and combined.
- In another bowl whisk together flour, baking powder, baking soda, and salt.
- Add half the dry ingredients to the butter mixture, mix on low, then blend in the pineapple juice, followed by the remaining dry ingredients until just combined.
- Use a 1.5-tablespoon scoop to portion dough and gently press one scoop over the fruit in each muffin cup.
- Bake for 10 to 12 minutes until the cookie edges are lightly golden and centers are just set.
- Cool in the pan for 5 minutes to set the topping.
- Run a thin knife around each cookie, invert the pan over a wire rack, and carefully lift to release the cookies.
- If any fruit sticks, spoon it back onto the warm cookies and let them cool 15 minutes before serving.
Notes
Thoroughly drying the pineapple and cherries prevents soggy tops and helps the cookies release cleanly. If the topping firms up before portioning, briefly rewarm it to keep it pourable. Avoid overbaking; these are best when slightly soft in the center and set at the edges. For neater tops, trim pineapple wedges so they sit flat and don’t overfill the cup. You can substitute crushed pineapple (well-drained) for easier fitting, or add a pinch of cinnamon to the topping for warmth. Store in an airtight container at room temperature for up to 2 days, or refrigerate up to 5 days; rewarm 10 seconds in the microwave to revive the caramel sheen.
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