Pineapple Upside Down Cookies

These delightful cookies transform the classic pineapple upside-down cake into a handheld treat featuring caramelized pineapple and a cherry center, offering a nostalgic dessert that's portable and easy to make.

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Prep Time 15

Cook Time 20

Total Time 35

Servings: 12 cookies

Course: Dessert, Snack

Cuisine: American

Calories: 180

Ingredients Method Nutrition Notes

Ingredients

For the cookie base

1 cup sugar
1/2 cup butter, softened Use room temperature butter for proper creaming.
1 large egg Use room temperature egg for better emulsification.
2 cups all-purpose flour
1 teaspoon baking powder
1/2 teaspoon salt

For the topping

1/2 cup brown sugar, for sprinkling Reduce to 3 tablespoons for less sweetness.
1 can pineapple slices, drained Drain pineapple very well and blot slices with a paper towel.
12 pieces Maraschino cherries Halve if they're large for even distribution.

For the glaze

1/4 cup brown sugar
1 tablespoon milk Use coconut milk for a coconut variation.

Method

Preparation

Preheat the oven to 350°F (175°C) and prepare a muffin tin by placing one pineapple slice and one maraschino cherry in the center of each cup.
In a large bowl, cream together the sugar and softened butter until smooth and slightly fluffy.
Beat in the egg until fully incorporated.
In another bowl, whisk together the flour, baking powder, and salt. Gradually add to the creamed mixture, stirring until combined.
In each prepared muffin cup, place the pineapple slice, set a cherry in its center, then sprinkle a little brown sugar over each pineapple.
Drop spoonfuls of cookie dough over each pineapple until the cups are nearly full.

Baking

Bake for 15 to 20 minutes, until the cookie tops are golden and a toothpick inserted near the center comes out with a few moist crumbs.

Nutrition

Serving: 1Calories: 180kcalCarbohydrates: 26gProtein: 2gFat: 8gSaturated Fat: 5gSodium: 150mgSugar: 10g

Notes

Serve cookies slightly warm with vanilla ice cream or whipped cream. Store cookies in an airtight container for up to 4 days, or freeze for longer storage. Rotate muffin tin halfway through baking for even browning.

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