ADVERTISEMENT

Pineapple Upside-Down Cookies: A Fun Twist on a Classic Dessert

There’s something undeniably nostalgic about a pineapple upside-down cake—the golden caramelized pineapples, the sweet burst of cherries, and the buttery cake base that makes every bite a delight. But what if you could capture all that magic in a cookie? That’s exactly what these Pineapple Upside-Down Cookies offer—a bite-sized version of the beloved dessert that’s perfect for sharing, gifting, or indulging in whenever you crave a tropical treat.

Print
clock clock iconcutlery cutlery iconflag flag iconfolder folder iconinstagram instagram iconpinterest pinterest iconfacebook facebook iconprint print iconsquares squares iconheart heart iconheart solid heart solid icon

Pineapple Upside-Down Cookies: A Fun Twist on a Classic Dessert

5 Stars 4 Stars 3 Stars 2 Stars 1 Star

No reviews

Love Pineapple Upside-Down Cake? 🍍🎂 Then you HAVE to try these Pineapple Upside-Down Cookies! 🍪✨ They have all the flavors of the classic dessert in a soft, chewy, handheld form! 🏝️ Buttery cookies, caramelized pineapple, and a cherry on top—what’s not to love? 🍒 Perfect for summer gatherings, tea time, or just because you deserve a treat. 😍 Bake up a batch and watch them disappear in minutes! Who’s grabbing one first? 👀💛 #TropicalDessert #PineapplePerfection #CookieTime #EasyBaking #HomemadeGoodness #DessertLovers #CherryOnTop #QuickAndDelicious #FruitFilledTreats #SweetEscape 🍪

  • Total Time: 27-30 minutes
  • Yield: 12 cookies

Ingredients

For the Cookie Base:

  • Unsalted Butter (½ cup, softened) – Gives the cookies their rich, buttery texture. If using salted butter, reduce the added salt.
  • Granulated Sugar (¾ cup) – Provides sweetness and helps with the cookie’s soft structure. Brown sugar can be used for a deeper caramel-like flavor.
  • Large Egg (1) – Binds the ingredients together and adds moisture. If allergic to eggs, substitute with a flax egg (1 tbsp ground flaxseed + 3 tbsp water).
  • Vanilla Extract (1 tsp) – Enhances the sweetness with warm, aromatic notes.
  • All-Purpose Flour (1 ¼ cups) – Forms the cookie’s structure. If needed, use a 1:1 gluten-free flour blend.
  • Baking Powder (½ tsp) – Helps the cookies rise slightly and stay soft.
  • Salt (¼ tsp) – Balances sweetness and enhances flavors.

For the Topping:

  • Brown Sugar (½ cup) – Caramelizes during baking, creating the signature upside-down effect.
  • Melted Butter (2 tbsp) – Helps the brown sugar create a rich, syrupy base.
  • Pineapple Rings (1 small can, cut into smaller pieces) – Provides the tropical fruitiness. Fresh pineapple works too but should be cut into small tidbits for even baking.
  • Maraschino Cherries (halved) – Adds a pop of color and sweetness. Fresh cherries or dried cranberries can be used as alternatives.

Instructions

1. Prepare the Cookie Dough

  • Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper or a silicone baking mat.
  • In a mixing bowl, cream together the softened butter and granulated sugar until light and fluffy. This can be done with an electric mixer or by hand using a whisk. Proper creaming ensures a soft and tender cookie.
  • Add the egg and vanilla extract, mixing until well combined. The batter should become smooth and slightly glossy.
  • In a separate bowl, whisk together the all-purpose flour, baking powder, and salt.
  • Gradually add the dry ingredients to the wet mixture, stirring just until a soft dough forms. Avoid overmixing, as this can lead to tough cookies.

2. Prepare the Topping

  • In a small bowl, mix the melted butter and brown sugar until smooth. This will create the caramelized topping for each cookie.
  • Spoon about 1 teaspoon of the brown sugar mixture onto the lined baking sheet, spacing them apart to allow room for cookie spreading.

3. Assemble the Cookies

  • Place a small piece of pineapple (or pineapple tidbits) on top of each brown sugar base.
  • Add a maraschino cherry half in the center of the pineapple for a classic touch.
  • Scoop about 1 ½ tablespoons of cookie dough, flatten it slightly with your hands, and place it over the pineapple and brown sugar mixture. Gently press the dough to cover the fruit, ensuring the edges seal the topping.

4. Bake the Cookies

  • Bake in the preheated oven for 12-15 minutes, or until the cookies turn golden around the edges.
  • Remove from the oven and let them cool on the baking sheet for 5 minutes before carefully transferring them to a wire rack. Allowing them to cool helps set the caramelized topping.

5. Serve and Enjoy

  • Once completely cooled, flip the cookies upside-down to reveal the beautiful pineapple-cherry topping. Enjoy as a snack, dessert, or party treat!

Notes

  • Dough too sticky? Chill it in the fridge for 10-15 minutes before handling. This makes it easier to shape.
  • Cookies spreading too much? Ensure your butter isn’t overly softened. Slightly cold butter helps cookies hold their shape.
  • Pineapple releasing too much juice? Pat the pineapple pieces dry with a paper towel before using. Too much moisture can cause soggy cookies.
  • Cookies sticking to the pan? Use parchment paper or a silicone baking mat to prevent sticking and make cleanup easier.
  • Want crispier edges? Bake for an extra 2 minutes, but watch carefully to prevent burning.
  • Author: Rosa
  • Prep Time: 15 minutes
  • Cook Time: 12-15 minutes

Why This Recipe is Perfect for Beginners

If you’re new to baking, this recipe is a fantastic starting point. It keeps things simple while teaching essential baking techniques like creaming butter and sugar, properly mixing dry and wet ingredients, and layering flavors for the perfect bite. Here’s why this recipe works so well for beginners:

  • Minimal Equipment Needed: No fancy cake pans or mixers required—just basic kitchen tools.
  • Easy-to-Follow Steps: Each component is straightforward, from making the dough to assembling the cookies.
  • Foolproof Flavors: Pineapple, brown sugar, and buttery cookies are a combination that’s hard to mess up. Even if your cookies aren’t perfect, they’ll still taste amazing!
  • Customizable: Whether you prefer fresh pineapple over canned, or want to add a coconut twist, this recipe allows for easy adjustments.

Ingredients and Substitutions

This recipe calls for a handful of pantry staples and a few fresh ingredients. Here’s what you’ll need and some handy alternatives:

For the Cookie Base:

  • Unsalted Butter (½ cup, softened) – Gives the cookies their rich, buttery texture. If using salted butter, reduce the added salt.
  • Granulated Sugar (¾ cup) – Provides sweetness and helps with the cookie’s soft structure. Brown sugar can be used for a deeper caramel-like flavor.
  • Large Egg (1) – Binds the ingredients together and adds moisture. If allergic to eggs, substitute with a flax egg (1 tbsp ground flaxseed + 3 tbsp water).
  • Vanilla Extract (1 tsp) – Enhances the sweetness with warm, aromatic notes.
  • All-Purpose Flour (1 ¼ cups) – Forms the cookie’s structure. If needed, use a 1:1 gluten-free flour blend.
  • Baking Powder (½ tsp) – Helps the cookies rise slightly and stay soft.
  • Salt (¼ tsp) – Balances sweetness and enhances flavors.

For the Topping:

  • Brown Sugar (½ cup) – Caramelizes during baking, creating the signature upside-down effect.
  • Melted Butter (2 tbsp) – Helps the brown sugar create a rich, syrupy base.
  • Pineapple Rings (1 small can, cut into smaller pieces) – Provides the tropical fruitiness. Fresh pineapple works too but should be cut into small tidbits for even baking.
  • Maraschino Cherries (halved) – Adds a pop of color and sweetness. Fresh cherries or dried cranberries can be used as alternatives.

Step-by-Step Instructions

1. Prepare the Cookie Dough

  • Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper or a silicone baking mat.
  • In a mixing bowlcream together the softened butter and granulated sugar until light and fluffy. This can be done with an electric mixer or by hand using a whisk. Proper creaming ensures a soft and tender cookie.
  • Add the egg and vanilla extract, mixing until well combined. The batter should become smooth and slightly glossy.
  • In a separate bowl, whisk together the all-purpose flour, baking powder, and salt.
  • Gradually add the dry ingredients to the wet mixture, stirring just until a soft dough forms. Avoid overmixing, as this can lead to tough cookies.

2. Prepare the Topping

  • In a small bowl, mix the melted butter and brown sugar until smooth. This will create the caramelized topping for each cookie.
  • Spoon about 1 teaspoon of the brown sugar mixture onto the lined baking sheet, spacing them apart to allow room for cookie spreading.

3. Assemble the Cookies

  • Place a small piece of pineapple (or pineapple tidbits) on top of each brown sugar base.
  • Add a maraschino cherry half in the center of the pineapple for a classic touch.
  • Scoop about 1 ½ tablespoons of cookie dough, flatten it slightly with your hands, and place it over the pineapple and brown sugar mixture. Gently press the dough to cover the fruit, ensuring the edges seal the topping.

4. Bake the Cookies

  • Bake in the preheated oven for 12-15 minutes, or until the cookies turn golden around the edges.
  • Remove from the oven and let them cool on the baking sheet for 5 minutes before carefully transferring them to a wire rack. Allowing them to cool helps set the caramelized topping.

5. Serve and Enjoy

  • Once completely cooled, flip the cookies upside-down to reveal the beautiful pineapple-cherry topping. Enjoy as a snack, dessert, or party treat!

Beginner Tips and Troubleshooting

Even the simplest recipes can sometimes go wrong. Here are some handy tips to ensure your Pineapple Upside-Down Cookies turn out perfect every time:

  • Dough too sticky? Chill it in the fridge for 10-15 minutes before handling. This makes it easier to shape.
  • Cookies spreading too much? Ensure your butter isn’t overly softened. Slightly cold butter helps cookies hold their shape.
  • Pineapple releasing too much juice? Pat the pineapple pieces dry with a paper towel before using. Too much moisture can cause soggy cookies.
  • Cookies sticking to the pan? Use parchment paper or a silicone baking mat to prevent sticking and make cleanup easier.
  • Want crispier edges? Bake for an extra 2 minutes, but watch carefully to prevent burning.

Serving Suggestions

These cookies are delicious on their own, but you can take them to the next level with these serving ideas:

  • With Ice Cream: Serve warm with a scoop of vanilla or coconut ice cream for a tropical treat.
  • With a Drizzle: Add a light caramel or white chocolate drizzle for extra indulgence.
  • Paired with Coffee or Tea: These cookies complement a hot cup of coffee, especially a latte or chai tea.

Storage and Make-Ahead Tips

  • Room Temperature: Store in an airtight container at room temperature for up to 3 days.
  • Refrigeration: If storing longer, keep them in the fridge for up to 5 days. Let them come to room temperature before eating.
  • Freezing: These cookies freeze well! Place them in a single layer on a baking sheet, freeze until firm, then transfer to a freezer-safe container. Store for up to 2 months. Thaw at room temperature before serving.

Final Thoughts: A Fun and Flavorful Treat

Pineapple Upside-Down Cookies are a delightful twist on a beloved classic, offering all the flavors of a pineapple upside-down cake in a portable, bite-sized form. Whether you’re a beginner baker looking for an easy recipe or a seasoned baker wanting to try something new, these cookies are a guaranteed crowd-pleaser. The combination of caramelized pineapple, sweet cherries, and buttery cookie dough creates an irresistible treat that’s sure to brighten any occasion.

Now it’s your turn! Have you tried making these cookies? What’s your favorite twist on the classic pineapple upside-down dessert? Share your experiences, tips, or variations in the comments below—I’d love to hear how they turned out for you! Happy baking!

ADVERTISEMENT

Leave a Comment

Recipe rating 5 Stars 4 Stars 3 Stars 2 Stars 1 Star

ADVERTISEMENT