If you’re a fan of pineapple upside-down cake and love chewy sugar cookies, then this Pineapple Upside-Down Sugar Cookies recipe is for you! These cookies take all the best elements of the classic cake—caramelized brown sugar, juicy pineapple, and a pop of cherry flavor—then shrink them down into bite-sized treats that are perfect for any occasion. Whether you’re making them for a summer barbecue, a holiday gathering, or just because you love pineapple desserts, these cookies are guaranteed to be a hit.
Why You’ll Love This Recipe
- Perfect Balance of Flavors – The rich caramelized brown sugar and butter mixture pairs beautifully with the tropical pineapple and the sweet sugar cookie base.
- Fun & Unique – A creative take on the classic pineapple upside-down cake but in a portable, easy-to-eat cookie form.
- Easy to Make – No special equipment needed, just a muffin tin and a handful of pantry staples.
- Beautiful Presentation – These cookies have a gorgeous golden topping with a bright cherry in the center, making them eye-catching at any event.
Ingredients Breakdown
To make these delicious pineapple upside-down sugar cookies, you’ll need a few basic ingredients. Here’s what they do in the recipe:
For the Topping:
- ¼ cup (½ stick) unsalted butter, melted – Helps caramelize the brown sugar for that signature upside-down cake flavor.
- ½ cup brown sugar – Adds sweetness and a deep, rich caramel-like flavor.
- 6 pineapple rings (cut in half) – Brings a fresh, juicy tropical flavor to the cookies.
- 6 maraschino cherries (cut in half) – Adds a bright pop of color and a sweet, fruity contrast.
For the Cookie Dough:
- ½ cup (1 stick) unsalted butter, softened – Creates a rich and tender cookie base.
- ¾ cup granulated sugar – Adds sweetness and structure to the cookies.
- 1 large egg – Helps bind the dough together for a soft, chewy texture.
- 1 teaspoon vanilla extract – Enhances the overall flavor.
- 1 ½ cups all-purpose flour – Provides structure for the cookies.
- ½ teaspoon baking soda – Helps with slight leavening and keeps the cookies soft.
- ¼ teaspoon salt – Balances the sweetness and enhances flavors.
Step-by-Step Instructions
Step 1: Prepare Your Baking Equipment
Start by preheating your oven to 350°F (175°C). If you’re using a muffin tin, grease it well to prevent sticking. If baking on a cookie sheet, line it with parchment paper to make cleanup easier.
Step 2: Make the Topping
In a small bowl, mix the melted butter and brown sugar together. Place about 1 teaspoon of this mixture in the bottom of each muffin cup (or drop onto a parchment-lined baking sheet if not using a tin).
Next, place half a pineapple ring on top of the brown sugar mixture in each cup. Add a cherry half to the center of the pineapple. This will create the signature look once the cookies are baked and flipped.
Step 3: Make the Sugar Cookie Dough
- In a mixing bowl, beat the softened butter and granulated sugar together until light and fluffy (about 2 minutes).
- Add in the egg and vanilla extract, then mix until well combined.
- In a separate bowl, whisk together the flour, baking soda, and salt.
- Gradually add the dry ingredients into the wet ingredients, mixing until just combined. Be careful not to overmix, as this can make the cookies tough.
Step 4: Assemble and Bake
Using a spoon or cookie scoop, drop about 2 tablespoons of cookie dough over each pineapple ring in the muffin tin. Lightly press down so it spreads evenly over the fruit.
Bake in the preheated oven for 12-15 minutes, or until the edges of the cookies are golden brown.
Step 5: Cool and Flip
Once out of the oven, let the cookies sit for about 5 minutes in the pan. Then, carefully invert the muffin tin onto a wire rack or plate. The cookies should pop right out with their beautiful caramelized pineapple topping showing.
Step 6: Serve & Enjoy!
Let the cookies cool for a few more minutes before serving. They are delicious warm, but also taste amazing at room temperature!
Tips for Success
- Use fresh pineapple – If you prefer, you can use fresh pineapple instead of canned for an even juicier taste.
- Grease the pan well – This helps ensure the cookies release easily without sticking.
- Don’t overbake – The cookies should be golden but still soft. Overbaking can lead to dryness.
- Serve with ice cream – These cookies pair wonderfully with vanilla ice cream for an extra indulgent treat.
Variations
- Add Coconut: Sprinkle shredded coconut over the brown sugar mixture before adding the pineapple for a more tropical vibe.
- Make it Mini: Use a mini muffin tin and cut pineapple rings into smaller chunks for bite-sized treats.
- Gluten-Free: Use a 1:1 gluten-free flour substitute to make these cookies gluten-free.
- Rum-Flavored: Add a teaspoon of rum extract or a splash of dark rum to the cookie dough for a richer, boozy twist.
Storing & Freezing
- Storing: Keep cookies in an airtight container at room temperature for up to 3 days.
- Refrigerating: If you want them to last longer, store them in the fridge for up to a week.
- Freezing: Freeze baked cookies in a single layer, then transfer to a freezer bag for up to 3 months. Thaw at room temperature before serving.
Final Thoughts
Pineapple Upside-Down Sugar Cookies are a delightful treat that bring together the best of both worlds: the nostalgic taste of upside-down cake and the classic chewy texture of a sugar cookie. They are fun to make, beautiful to serve, and absolutely delicious to eat!
Have you tried making these cookies? Let me know in the comments how they turned out! 🍍🍪