1. Can I use fresh pineapple instead of canned pineapple for these cookies?

Yes, you can use fresh pineapple, but keep in mind that canned pineapple tends to be sweeter and easier to work with in this recipe. If using fresh pineapple, make sure to cut it into rings and drain it thoroughly to avoid excess moisture.

2. Can I make Pineapple Upside Down Sugar Cookies ahead of time?

Absolutely! You can prepare the cookie dough in advance and refrigerate it for up to 24 hours before baking. This allows the flavors to meld together, and the dough will be easier to handle when you’re ready to bake. You can also assemble the cookies, store them in the fridge, and bake them the next day.

3. How do I store leftover Pineapple Upside Down Sugar Cookies?

Store your leftover cookies in an airtight container at room temperature for up to 7 days. They’re best enjoyed within the first 2-3 days for maximum freshness. If you want to extend their shelf life, consider freezing them.

4. Can I make a smaller version of Pineapple Upside Down Sugar Cookies?

Yes, you can make mini versions by using a mini muffin tin and smaller pineapple chunks. Just be sure to adjust the baking time, starting at around 8 minutes and checking for doneness. Using a smaller scoop for the dough will also help create the perfect bite-sized cookies

Pineapple Upside Down Sugar Cookies: A Sweet and Fun Treat

Name: Pineapple Upside Down Sugar Cookies
Prep time: 15 min
Cook time: 9 min
Total time: 24 min
Cuisine: American
Ingredients: 1/2 cup Butter (softened); 1/2 cup Granulated Sugar (100g); 1 large Egg; 1 teaspoon Vanilla Extract; 1/2 cup Powdered Sugar (65g); 1/4 cup Vegetable Oil; 1/2 teaspoon Baking Soda; 1/2 teaspoon Cream of Tartar; 2 cups All-Purpose Flour (240g); 6 tablespoons Butter (melted); 1 cup Brown Sugar (214g); Pineapple Rings (drained); Maraschino Cherries (drained)

Description

Pineapple Upside Down Sugar Cookies are a delightful dessert that brings the flavors of the classic pineapple upside-down cake into a fun, easy-to-make cookie form. These soft, chewy cookies are topped with a juicy pineapple ring and a vibrant maraschino cherry, making them perfect for summer gatherings or any occasion.

Ingredients

Scale

1/2 cup Butter (softened)
1/2 cup Granulated Sugar (100g)
1 large Egg
1 teaspoon Vanilla Extract
1/2 cup Powdered Sugar (65g)
1/4 cup Vegetable Oil
1/2 teaspoon Baking Soda
1/2 teaspoon Cream of Tartar
2 cups All-Purpose Flour (240g)
6 tablespoons Butter (melted)
1 cup Brown Sugar (214g)
Pineapple Rings (drained)
Maraschino Cherries (drained)

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Instructions

Preheat the oven to 350°F (175°C).
In a small mixing bowl, combine ½ cup of melted butter with 1 cup of brown sugar and stir until fully combined.
Drain the pineapple rings and set them aside.
Place 1 tablespoon of the brown sugar butter mixture into each well of the muffin tin, then top with 1 pineapple ring and place a maraschino cherry in the center of each pineapple ring.
Cream together softened butter and granulated sugar until light and fluffy.
Add the egg and vanilla extract, and continue to beat for 2-3 minutes.
Gradually add the vegetable oil, powdered sugar, and dry ingredients (flour, baking soda, and cream of tartar). Mix until fully combined.
Scoop out cookie dough using a #24 cookie scoop, flatten to about 3 inches in diameter, and place it on top of the pineapple ring and cherry, pressing the dough into the sides of the muffin tin.
Bake for 8-10 minutes, or until the edges are golden brown and the center is no longer glossy.
Remove from the oven and flip the pan onto a parchment-lined cookie sheet. Allow cookies to cool before serving.

Notes

Store cookies in an airtight container for up to 7 days.
For a fun variation, try substituting pineapple with fresh peaches or adding a sprinkle of shredded coconut.
If using fresh pineapple, ensure it is fully drained to avoid excess moisture.

Prep Time: 15 minutes
Cook Time: 9 minutes
Category: Dessert
Method: Baking
Cuisine: American

Nutrition

Serving Size: 1 cookie
Calories: 210
Sugar: 23g
Sodium: 150mg
Fat: 10g
Saturated Fat: 5g
Unsaturated Fat: 3g
Trans Fat: 0g
Carbohydrates: 28g
Fiber: 1g
Protein: 1g
Cholesterol: 20mg