Pineapple Upside Sugar Cookies Recipe
If you’re in the mood for something uniquely delightful that combines the tropical charm of pineapple with the comforting sweetness of sugar cookies, you are absolutely going to love this Pineapple Upside Sugar Cookies Recipe. It’s like a mini vacation for your taste buds with every bite – the buttery cookie base mingling perfectly with caramelized brown sugar and juicy pineapple slices topped with vibrant maraschino cherries. These cookies are not only a feast for the palate but also a cheerful, colorful treat that’s sure to brighten up any day or party.
Ingredients You’ll Need
This recipe calls for simple yet indispensable ingredients that come together beautifully to create those tender, flavorful cookies with that irresistible pineapple upside flair. Each ingredient plays its part, from the creamy butter that gives richness, to the sour cream which keeps the texture moist and soft, and of course, the pineapple and cherries for that nostalgic, summery touch.
- 1 cup butter (room temperature): Provides a rich, creamy base that makes the cookies tender and buttery.
- 1 ½ cups granulated sugar: Sweetens the dough and helps achieve a light, fluffy texture.
- 2 eggs: Bind the ingredients and add moisture for a soft cookie crumb.
- 2 teaspoons vanilla extract: Infuses warm, aromatic flavor that complements the pineapple beautifully.
- ½ cup sour cream: Adds tenderness and a slight tang that balances the sweetness.
- 3 cups all-purpose flour: Forms the sturdy but soft cookie structure.
- 1 teaspoon baking powder: Helps the cookies rise lightly for just the right fluffiness.
- 1 teaspoon cornstarch: Contributes to a soft, cakey texture.
- ½ teaspoon salt: Enhances all the flavors and balances the sweetness.
- 13 canned pineapple slices: The star of the show, they bring juicy, tropical flavor in every cookie.
- 13 maraschino cherries: Adds a pop of color and a sweet, fruity bite on top.
- ½ cup melted butter: Used with brown sugar to create a sticky, caramel-like base.
- 1 cup packed light brown sugar: Offers deep, molasses-rich sweetness that caramelizes wonderfully.
How to Make Pineapple Upside Sugar Cookies Recipe
Step 1: Preheat and Prepare the Pan
Start by heating your oven to a cozy 350°F (175°C). Lightly grease a mini round cake pan to ensure those cookies slide out easily after baking. This sets the stage for your pineapple upside cookies to develop that golden crust and caramelized base perfectly.
Step 2: Cream Butter and Sugar
In a large bowl, cream the softened butter and granulated sugar together until the mixture is fluffy and light. This process incorporates air into the dough, which is key for soft, tender cookies with just the right bite.
Step 3: Add Eggs, Vanilla, and Sour Cream
Now, mix in the eggs, vanilla extract, and sour cream until smooth and fully combined. The eggs provide structure, vanilla enhances the flavor depth, and sour cream keeps these cookies irresistibly moist.
Step 4: Combine Dry Ingredients and Form Dough
Gradually sift in the all-purpose flour, baking powder, cornstarch, and salt. Stir gently until a soft dough forms. This careful combining makes sure your cookies are perfectly tender without being dense.
Step 5: Prepare Brown Sugar Mixture
In a separate bowl, whisk together the melted butter and packed light brown sugar. This luscious mixture will create that signature caramelized bottom once baked, echoing the classic pineapple upside-down cake experience.
Step 6: Assemble the Cookies
Spoon about a tablespoon of the brown sugar and butter mixture into each cavity of your mini cake pan. Then, top each with a canned pineapple slice, pressing a maraschino cherry right into the center for that eye-catching detail and burst of sweetness.
Step 7: Top with Cookie Dough
Add roughly 3 tablespoons of the cookie dough over each pineapple slice, pressing gently so the dough covers the fruit but remains airy enough to bake through evenly.
Step 8: Bake and Cool
Bake your cookies for approximately 25 minutes or until they turn a lovely golden brown shade. Let them cool in the pan for about 10 minutes, which helps the caramel set. Then carefully invert them onto wax paper to cool completely, revealing that stunning pineapple upside design.
How to Serve Pineapple Upside Sugar Cookies Recipe
Garnishes
While these cookies are already beautiful and flavorful on their own, a light dusting of powdered sugar or a drizzle of vanilla glaze can elevate their appearance and add a gentle sweetness that doesn’t overpower the pineapple’s tang.
Side Dishes
Pair these cookies with a scoop of vanilla ice cream or a dollop of whipped cream for an indulgent dessert experience. They also go surprisingly well with a fresh fruit salad that echoes their tropical notes.
Creative Ways to Present
For a festive touch, arrange the cookies on a decorative platter with fresh mint leaves scattered for a pop of green. Serving them alongside a sweet tropical punch or a bubbly sparkling lemonade can turn your gathering into a mini luau!
Make Ahead and Storage
Storing Leftovers
Keep any leftover Pineapple Upside Sugar Cookies in an airtight container at room temperature to retain their softness. They stay fresh for about 3 to 4 days, perfect if you want to enjoy a taste over multiple days.
Freezing
You can freeze these cookies by wrapping each one individually in plastic wrap, then placing them in a resealable freezer bag. Frozen cookies can last up to 2 months and make for a delightful treat anytime you crave something sweet and nostalgic.
Reheating
To revive that freshly baked warmth, simply warm the cookies in a preheated oven at 300°F (150°C) for about 5 to 7 minutes. This brings out the buttery aroma again and softens the cookies without drying them out.
FAQs
Can I use fresh pineapple instead of canned slices?
Fresh pineapple can work, but canned pineapple slices tend to hold their shape better during baking and have consistent sweetness and moisture levels, making your cookies turn out just right.
Is it necessary to use sour cream in the dough?
Sour cream adds moisture and a slight tang that balances the sweetness, but if you don’t have it on hand, plain yogurt or buttermilk can be useful substitutes.
What size should the mini round cake pan be?
The ideal mini cake pan cavities are about 3 inches in diameter, perfect for single-serving cookies that highlight the pineapple and cherry beautifully.
Can I make these gluten-free?
Yes! Use a gluten-free all-purpose flour blend that includes xanthan gum to help the dough maintain its structure and texture.
How do I prevent the cookies from sticking to the pan?
Lightly greasing the pan and allowing the cookies to cool before inverting are key steps. You can also use parchment paper liners designed for mini cake pans for easier removal.
Final Thoughts
Trying out this Pineapple Upside Sugar Cookies Recipe means inviting a playful, tropical twist into your cookie repertoire that will have friends and family swooning over their charming look and delicious taste. These cookies are a wonderfully fun way to brighten any occasion or simply treat yourself to an amazing homemade dessert. Go ahead and give them a try — your kitchen will thank you!
Print
Pineapple Upside Sugar Cookies Recipe
- Total Time: 40 minutes
- Yield: 13 servings 1x
Description
These Pineapple Upside Down Sugar Cookies combine the tropical sweetness of pineapple and maraschino cherries with classic sugar cookie dough, baked to golden perfection. Each mini cookie features a caramelized brown sugar and butter base topped with a pineapple slice and cherry, creating a delightful twist on the traditional upside-down cake in cookie form. Perfect for a sweet treat or a festive gathering.
Ingredients
Cookie Dough
- 1 cup butter (room temperature)
- 1 ½ cups granulated sugar
- 2 eggs
- 2 teaspoons vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 teaspoon baking powder
- 1 teaspoon cornstarch
- ½ teaspoon salt
Topping
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ cup melted butter
- 1 cup packed light brown sugar
Instructions
- Preheat Oven and Prepare Pan: Preheat your oven to 350°F (175°C). Lightly grease a mini round cake pan to prevent sticking and ensure easy removal of the cookies.
- Cream Butter and Sugar: In a large mixing bowl, use a hand mixer or stand mixer to cream together the room temperature butter and granulated sugar until the mixture is fluffy and light, which helps create a tender cookie texture.
- Add Wet Ingredients: Mix in the eggs, vanilla extract, and sour cream until completely combined, creating a smooth batter that will lend moisture and richness to your cookies.
- Incorporate Dry Ingredients: Gradually add the all-purpose flour, baking powder, cornstarch, and salt into the wet mixture. Stir until a cohesive dough forms, being careful not to overmix to maintain a tender crumb.
- Prepare Brown Sugar Mixture: In a separate small bowl, combine the melted butter and light brown sugar. Mix well until smooth to create a caramel-like topping base.
- Add Toppings to Pan: Spread about 1 tablespoon of the brown sugar mixture evenly into each cavity of the mini cake pan. Then place one pineapple slice atop each brown sugar layer, pressing slightly. Center a maraschino cherry on each pineapple slice for the classic look and sweet flavor.
- Top with Cookie Dough: Spoon roughly 3 tablespoons of cookie dough over each pineapple slice, gently pressing the dough to cover the fruit but avoiding squeezing the cherry out of place.
- Bake the Cookies: Place the pan in the preheated oven and bake for approximately 25 minutes, or until the cookies turn golden brown and are set around the edges.
- Cool and Serve: Allow the cookies to cool in the pan for 10 minutes to set the toppings and prevent breaking. Then carefully turn out the cookies onto wax paper or a wire rack to cool completely before serving.
Notes
- Make sure the butter is at room temperature to ensure proper creaming with the sugar.
- Use canned pineapple slices for convenience and consistent size; drain well to avoid excess moisture.
- If you don’t have a mini round cake pan, mini muffin pans can be used as an alternative, adjusting dough quantity accordingly.
- For a stronger caramel flavor, you can use dark brown sugar instead of light brown sugar.
- Allow cookies to cool completely before removing from the pan to keep toppings intact.
- Prep Time: 15 minutes
- Cook Time: 25 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
