Pineapple Upside Down Cookies

This recipe is a Laura’s Bake Lab staple - taking a classic dessert and putting it in cookie form. This time I’m doing it with pineapple upside down cake. These Pineapple Upside Down Cookies feature a buttery sugar cookie baked atop a sugared pineapple ring and maraschino cherry to give all the flavors of a pineapple upside down cake in a fun handheld form.

Prepare the Cookie Dough

Start by preparing the cookie dough. It will need to chill before baking.

1. In a medium bowl, whisk together all purpose flour, cornstarch, baking soda, and salt. Set aside.

2. In a large bowl using a handheld or stand mixer fitted with the paddle attachment, beat softened butter on medium speed until smooth. Add granulated and brown sugars and continue to mix until light and fluffy.

3. Add one egg, pineapple juice, and vanilla and mix until combined. The mixture may look a little lumpy, but that's okay.

4. Add the dry ingredients to the wet ingredients and mix until just combined.

Cover and refrigerate the dough for 30 minutes.

Prepare the Pineapple

Line two baking sheets with parchment paper. Pat 16 pineapple rings dry and place them on the prepared baking sheets at least one inch apart. Place a halved cherry in the center of each pineapple ring with the uncut side down.

To make the sugar mixture that will go on the pineapples, whisk together melted butter, brown sugar, and bourbon or rum (optional, but adds another layer of flavor).

Brush the sugar mixture over the pineapples, making sure you use all of it.

Assemble the Cookies

Divide the chilled dough into 16 equal portions. Roll the dough into balls and place them on the sugared pineapples, pressing down and flattening the dough so it mostly covers the pineapples like in the image below.

Bake the Cookies

Bake the cookies at 375°F for 16-18 minutes until the edges start to brown and the tops begin to crack. If you want uniform looking cookies like in the image below, use the back of a spoon to flatten the cookies immediately after they are removed from the oven.

Allow the cookies to cool on the pan for at least 10 minutes before using a spatula to transfer them to a wire cooling rack (pineapple side up) to cool completely. Store leftover cookies in an airtight container in the refrigerator for 3-5 days.

cookies

Yield: 16

Author: Laura's Bake Lab

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Pineapple Upside Down Cookies

Buttery sugar cookies baked atop sweetened pineapples and a maraschino cherry make for a handheld version of a pineapple upside down cake.

Prep time: 20 MinCook time: 16 MinInactive time: 30 MinTotal time: 1 H & 6 M

Ingredients

Cookie Dough

• 2 and 1/2 cups all purpose flour
• 2 tsp cornstarch
• 1 tsp baking soda
• 1/4 tsp salt
• 3/4 cup unsalted butter, softened to room temperature
• 3/4 cup granulated sugar
• 1/4 cup brown sugar
• 1 egg, room temperature
• 2 Tbsp pineapple juice
• 1 and 1/2 tsp vanilla extract

Pineapples

• 16 pineapple rings
• 8 maraschino cherries, cut in half
• 2 Tbsp melted butter
• 1/3 cup brown sugar
• 1 Tbsp bourbon or rum (optional)

Instructions

1. In a medium bowl, whisk together the flour, cornstarch, baking soda, and salt. Set aside.
2. In a large bowl using a handheld or stand mixer fitted with the paddle attachment, beat the softened butter on medium speed until smooth. Add the granulated and brown sugar and continue to mix until light and fluffy.
3. Add the egg, pineapple juice, and vanilla and mix until combined. The mixture may look a little lumpy, but that's okay.
4. Add the dry ingredients to the wet ingredients and mix until just combined. Cover and refrigerate the dough for 30 minutes.
5. Meanwhile, preheat the oven to 375°F. Line two baking sheets with parchment paper.
6. Pat the pineapple rings dry. Place them on the prepared baking sheets at least 1 inch apart. Place the halved cherries in the center of the pineapple rings, uncut side down.
7. In a small bowl, whisk together the melted butter, brown sugar, and bourbon or rum (if using) until smooth. Brush the sugar mixture over the pineapples.
8. Divide the chilled dough into 16 equal portions. Roll the dough into balls and place them on the sugared pineapples, pressing down and flattening the dough so it mostly covers the pineapples.
9. Bake the cookies for 16-18 minutes until the edges are a light golden brown and the tops begin to crack. If desired, use the back of a spoon to flatten the cookies immediately after they are removed from the oven for a more uniform appearance. Allow the cookies to cool on the pan for at least 10 minutes before using a spatula to transfer them to a wire cooling rack (pineapple side up) to cool completely.
10. Store leftover cookies in an airtight container in the refrigerator for 3-5 days.

https://www.laurasbakelab.com/blog/pineapple-upside-down-cookies

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