Pineapple Upside Down Cookies

By The Stay At Home Chef
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Ingredients

2 (20-ounce can) pineapple rings (drained)
9 maraschino cherries (halved)
1/2 cup brown sugar
1 cup unsalted butter (softened)
3/4 cup brown sugar
1/2 cup granulated sugar
2 large eggs
1 teaspoon vanilla extract
3 cups all-purpose flour
1 teaspoon baking powder
1 teaspoon baking soda
1/2 teaspoon salt

  • Prep Time15mins
  • Cook Time25mins
  • Servings18
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Instructions

Preheat your oven to 400°F (204°C). Line two baking sheets with parchment paper or silicone baking mats.

Drain the juice from 2 (20-ounce can) pineapple rings. Use paper towels or a clean dish towel to pat them dry. Place the rings, evenly spaced, on the prepared baking sheets, about 9 per pan. Place a halved maraschino cherry in the center. Sprinkle each pineapple ring with a small spoonful of brown sugar, about 1 1/2 teaspoons per ring.

Bake in the oven for about 10 minutes, until the brown sugar has candied onto the pineapple. Remove trays from oven and let cool while you make the cookie dough.

In a large mixing bowl use a hand mixer to beat 1 cup unsalted butter (softened), 3/4 cup brown sugar, and 1/2 cup granulated sugar until smooth and creamy, about 3 minutes. It should become pale, fluffy, and visibly lighter in color.

Add 2 large eggs, and 1 teaspoon vanilla extractBeat on low speed until just combined, about 30 seconds.

Add 3 cups all-purpose flour, 1 teaspoon baking powder, 1 teaspoon baking soda, and 1/2 teaspoon salt. Mix until just combined.

Take about 2 tablespoons of the dough and form a ball, and set it on top of each candied pineapple ring. Gently press the dough to flatten it just enough to adhere it to the ring.

Return the pans to the oven to bake the cookies for 12 to 14 minutes, until the tops of the cookies are golden brown.

Allow the cookies to cool on the baking sheets for 15 minutes before serving warm. Alternatively, transfer them to a wire rack to cool completely.

Dessert
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