Pineapple Upside Down Cookies mix the classic dessert flavors into a fun and easy-to-make treat. With their sweet pineapple topping and buttery cookie base, these cookies offer a delightful alternative to the traditional cake version. You can impress your friends and family with these delightful bites that are perfect for any occasion, from casual snacks to special gatherings.
Why We Love This Pineapple Upside Down Cookies
This recipe brings all the nostalgia of pineapple upside-down cake into a cookie form, making it easier to enjoy and share. You get the perfect balance of sweetness from the pineapple and a buttery richness from the cookie itself. Each bite offers a delightful texture with a crisp edge and a soft center, creating a perfect treat for any time of the day. Plus, these cookies are incredibly easy to make, even for beginner bakers. The fun, fruity flavor captures the essence of summer and tropical vibes, giving you a taste of paradise right in your own kitchen. You can customize them easily, making them versatile enough to suit your preferences or dietary needs. Overall, you’ll love how simple yet delicious these cookies can be, becoming a staple in your baking repertoire.
Ingredients for Pineapple Upside Down Cookies
- 1 cup unsalted butter, softened
- 1 cup brown sugar, packed
- 1 large egg
- 1 teaspoon vanilla extract
- 2 cups all-purpose flour
- 1 teaspoon baking soda
- ½ teaspoon salt
- 1 cup crushed pineapple, drained
- 1 cup maraschino cherries, halved
- ½ cup finely chopped pecans or walnuts (optional)
Directions
- Preheat your oven to 350°F (175°C). Prepare a baking sheet by lining it with parchment paper.
- In a large mixing bowl, cream the softened butter and brown sugar together until the mixture is light and fluffy.
- Add the egg and vanilla extract to the butter-sugar mixture. Beat until well combined.
- In another bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until just combined.
- Fold in the crushed pineapple gently into the dough until evenly distributed.
- Scoop out tablespoons of cookie dough onto the prepared baking sheet, spacing them about 2 inches apart.
- Make an indentation in the center of each cookie dough ball using your thumb. Place a cherry half inside the indentation, followed by a sprinkle of chopped nuts if desired.
- Bake in the preheated oven for 12-14 minutes, or until the cookies are lightly golden around the edges.
- Remove the baking sheet from the oven and allow the cookies to cool for a few minutes before transferring them to a wire rack to cool completely.
How to Serve Pineapple Upside Down Cookies
Pineapple upside-down cookies are a delightful treat that can be served in many ways. You can enjoy them warm or at room temperature, and they pair wonderfully with a scoop of vanilla ice cream, creating a perfect dessert for summer gatherings. For a fun presentation, stack them in a clear glass jar or on a decorative plate beside fresh fruit for a colorful display. A light dusting of powdered sugar or a drizzle of cream cheese frosting can add a touch of elegance, perfect for parties or occasions. You might also consider serving these cookies alongside a tropical fruit salad or a refreshing beverage like coconut water or iced tea. Guests will appreciate the tropical twist and variety in flavors. Additionally, you can pack them in lunch boxes or as a snack for road trips to share the joy of these cookies wherever you go.
Expert Tips for Pineapple Upside Down Cookies
To achieve the best results with your pineapple upside-down cookies, keep a few expert tips in mind. First, ensure that your butter is adequately softened before mixing; this helps create a creamy texture that holds air, resulting in lighter cookies. Use fresh, high-quality ingredients, especially for the pineapple. Opt for crushed pineapple packed in juice rather than syrup for a fresher flavor and to keep cookies from becoming overly sweet. Pay attention to your baking time; overbaking can lead to dry cookies. A simple trick involves checking them a minute or two earlier than recommended for that perfect balance. Consider experimenting with different mix-ins, such as coconut flakes for added texture or a dash of cinnamon for warmth. Finally, allow the cookies to cool completely on a wire rack before storing them to prevent excess moisture. These tips will ensure that you create a batch of pineapple upside-down cookies that are irresistible and full of flavor.
How to Store Pineapple Upside Down Cookies
Proper storage will keep your pineapple upside-down cookies fresh and delicious for days. Once they have completely cooled, place them in an airtight container at room temperature. They will stay fresh for about 3–5 days. If you want to store them for a longer period, consider freezing them. To freeze, wrap each cookie tightly in plastic wrap or place them in a freezer-safe bag, ensuring as much air as possible is removed. These cookies can be frozen for up to three months. When you’re ready to enjoy them, just defrost them at room temperature or warm them in the oven for a few minutes to restore their original texture. Storing and freezing your cookies properly ensures that you can enjoy these delightful treats even later on, without compromising their taste.
Variations of Pineapple Upside Down Cookies
You can easily customize pineapple upside-down cookies to fit your tastes or dietary needs. Here are some fun variations to consider. First, for a healthier twist, substitute coconut flour or almond flour for all-purpose flour. This adds a nutty flavor while keeping the cookies gluten-free as long as you follow the right recipe. You can also add other fruits like mangoes or diced peaches for a tropical fruit medley. If you want a nutty flavor without using traditional nuts, try mixing in sunflower seeds or chia seeds. For a more decadent treat, drizzle dark chocolate or white chocolate over the cookies after baking for extra sweetness. You can even add spices like nutmeg or ginger for a creative spin that complements the tropical flavors. Lastly, to celebrate special holiday occasions, consider adding colored sprinkles on top or incorporating festive flavors, turning this yummy cookie into a seasonal delight. These variations allow for endless experimentation and fun in your baking adventures.
FAQ about Pineapple Upside Down Cookies
You may have some questions about making pineapple upside-down cookies, and there are a few common queries that often arise. One common question is whether you can use fresh pineapple instead of canned. Yes, you can use fresh pineapple; just make sure to chop it finely and drain any excess juice. Another frequently asked question is if these cookies will turn out well if made ahead of time. Absolutely! They store well and can maintain their flavor for several days. If you’re wondering if these cookies freeze well, they do! Just follow the proper freezing instructions, and you can enjoy them for a long time beyond baking day. Many also ask whether these cookies can be made without eggs. You can replace the egg with a flaxseed egg (one tablespoon of ground flaxseed mixed with three tablespoons of water) for a vegan version. Finally, some wonder about serving sizes. Typically, this recipe yields about 24 cookies, making it perfect for sharing or enjoying over several days. Enjoy your baking adventure with these cookies!

Pineapple Upside Down Cookies
Ingredients
Cookie Base
- 1 cup unsalted butter, softened
- 1 cup brown sugar, packed
- 1 large egg
- 1 teaspoon vanilla extract
- 2 cups all-purpose flour
- 1 teaspoon baking soda
- ½ teaspoon salt
Toppings
- 1 cup crushed pineapple, drained Use pineapple packed in juice for best flavor.
- 1 cup maraschino cherries, halved
- ½ cup finely chopped pecans or walnuts (optional) Use nuts to enhance flavor and texture.
Instructions
Preparation
- Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
- In a large mixing bowl, cream the softened butter and brown sugar together until light and fluffy.
- Add the egg and vanilla extract to the butter-sugar mixture and beat until well combined.
- In another bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until just combined.
- Fold in the crushed pineapple gently into the dough until evenly distributed.
- Scoop out tablespoons of cookie dough onto the prepared baking sheet, spacing them about 2 inches apart.
- Make an indentation in the center of each cookie dough ball using your thumb, and place a cherry half inside the indentation. Add chopped nuts if desired.
Baking
- Bake in the preheated oven for 12-14 minutes or until the cookies are lightly golden around the edges.
- Remove from the oven and let the cookies cool for a few minutes before transferring them to a wire rack to cool completely.
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