PINEAPPLE UPSIDE DOWN SUGAR COOKIES

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Ah, a brilliant mashup! Pineapple Upside Down Cookies capture the iconic flavors of the classic cake in a soft, chewy, portable cookie form. These are a guaranteed showstopper.

Pineapple Upside Down Cookies

Yield: 12-14 large cookies
Prep Time: 25 minutes (+ 30-60 min chill)
Bake Time: 12-14 minutes

Ingredients

For the Pineapple Topping:

· 6-7 rings of canned pineapple (in juice, not heavy syrup), patted very dry
· 12-14 maraschino cherries, patted very dry
· ¼ cup (56g) unsalted butter, melted
· ½ cup (100g) light brown sugar, packed
· Pinch of salt

For the Sugar Cookie Dough:

· 2 ¼ cups (281g) all-purpose flour
· ½ teaspoon baking powder
· ¼ teaspoon baking soda
· ½ teaspoon salt
· ¾ cup (170g) unsalted butter, softened to room temperature
· ¾ cup (150g) granulated sugar
· ¼ cup (50g) light brown sugar, packed
· 1 large egg + 1 large egg yolk, room temperature
· 2 teaspoons vanilla extract (or 1 tsp vanilla + 1 tsp coconut extract for tropical flair)
· 1 tablespoon reserved pineapple juice (from the can)

Instructions

Part 1: Prepare the Pan & Topping

  1. Prep: Preheat oven to 350°F (175°C). Line a light-colored metal baking sheet with parchment paper. Do not use a dark sheet, as the bottom sugar will burn.
  2. Make Caramel Glue: In a small bowl, stir together the ¼ cup melted butter, ½ cup brown sugar, and pinch of salt. Spread about 2 teaspoons of this mixture into a 2-3 inch circle on the parchment paper for each cookie you plan to bake (space them 3 inches apart).
  3. Add Fruit: Place one well-dried pineapple ring on top of each butter-sugar circle. Place a dried maraschino cherry in the center of each ring. Set the pan aside.

Part 2: Make the Cookie Dough

  1. Whisk Dry Ingredients: In a medium bowl, whisk together flour, baking powder, baking soda, and salt.
  2. Cream Wet Ingredients: In a large bowl, using a hand mixer or stand mixer, cream the softened butter, granulated sugar, and ¼ cup brown sugar together on medium-high speed for 2-3 minutes until light and fluffy.
  3. Add Eggs & Flavor: Beat in the whole egg, then the egg yolk, one at a time, scraping down the bowl. Mix in the vanilla extract and 1 tbsp pineapple juice.
  4. Combine: On low speed, gradually add the dry ingredients to the wet ingredients, mixing just until no flour streaks remain. Do not overmix.

Part 3: Assemble & Bake

  1. Chill Dough (Optional but Recommended): For thicker cookies that won’t overspread, cover and chill the dough for 30-60 minutes.
  2. Top the Fruit: Using a large cookie scoop (about 3 tbsp of dough), place a ball of dough directly on top of each pineapple ring on your prepared sheet. Use slightly damp fingers to gently press and flatten the dough ball so it mostly covers the pineapple ring, leaving just a tiny edge of fruit visible.
  3. Bake: Bake for 12-14 minutes, or until the cookie edges are set and lightly golden. The centers will look soft.
  4. The Critical Flip: Let cookies cool on the baking sheet for exactly 2 minutes. This allows the caramel to set slightly. Then, carefully flip each cookie over onto a wire rack or another piece of parchment. If any caramel or fruit sticks to the pan, use a spatula to scrape it onto the cookie. Let cool completely.

Essential Tips for Success:

· DRY THE FRUIT: This is non-negotiable. Pat the pineapple rings and cherries extremely dry with layers of paper towels. Any extra moisture will make the caramel soupy and the cookies soggy.
· Pineapple Size: If your pineapple rings are very large, you can cut them in half and make “half-moon” cookies, or use pineapple tidbits/well-dried crushed pineapple for a simpler approach.
· Brown Sugar Press: When making the caramel circles, press the brown sugar into the melted butter on the parchment. It should look like wet sand.
· The 2-Minute Flip: Flipping too soon = hot caramel runs everywhere. Flipping too late = caramel hardens and sticks to the parchment. 2 minutes is the sweet spot.
· Storage: Store in a single layer or with parchment between layers at room temperature for up to 3 days. They are best enjoyed within 48 hours.

Variation: Pineapple Upside Down Drop Cookies

For a simpler, faster version (no flipping!):

  1. Finely chop ½ cup of well-dried pineapple rings and ¼ cup of maraschino cherries.
  2. Fold them into the cookie dough along with ½ cup of toasted chopped pecans (optional).
  3. Scoop and bake as normal cookies at 350°F for 10-12 minutes. The fruit will be baked inside.

Enjoy these stunning, flavor-packed cookies that bring all the nostalgic joy of the classic dessert!

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