Pineapple Upside Down Sugar Cookies Recipe
Get ready to swoon over these Pineapple Upside Down Sugar Cookies! Imagine adorable, personal-sized treats that bring together the nostalgia of a classic pineapple upside down cake and the sweet simplicity of a homemade sugar cookie. Each cookie is buttery and tender, topped with a glistening pineapple ring, a cherry jewel, and that irresistible caramelized brown sugar coating. If you’ve ever wanted a dessert that’s equally beautiful and scrumptious, this is your ticket to paradise—one bite, and you’ll see why these cookies are an all-time favorite in my kitchen!
Ingredients You’ll Need
Ingredients You’ll Need
The line-up for Pineapple Upside Down Sugar Cookies couldn’t be simpler, but every ingredient adds a special something—flavor, tenderness, richness, or color. Let’s walk through these basics that deliver a wow-worthy cookie every time.
- Butter (room temperature): Softened butter creates that dreamy, melt-in-your-mouth sugar cookie base and helps whip the dough up ultra-light.
- Granulated sugar: Adds sweetness and gives the cookies their classic crumbly exterior.
- Eggs: Give the dough structure, richness, and an even bake.
- Vanilla extract: Just a couple teaspoons bring out warmth and depth in the sugar cookie dough.
- Sour cream: Pushes the cookies into ultra-tender territory and keeps them perfectly moist.
- All-purpose flour: The backbone of the dough, so everything holds together just right.
- Baking powder: Gives these thick cookies a gentle lift for a pillowy center.
- Cornstarch: The secret to a soft and tender crumb—don’t skip it!
- Salt: Enhances all the sweet, fruity, and buttery flavors in the cookie.
- Canned pineapple slices: Sweet-tart pineapple makes every bite juicy and sunshiny.
- Maraschino cherries: One per cookie adds a pop of bright color and classic, kid-in-a-candy-store flavor.
- Butter (melted): Mixed with brown sugar to create that shimmering, caramel-like topping.
- Light brown sugar (packed): Caramelizes as the cookies bake to form an irresistible sticky-sweet layer.
How to Make Pineapple Upside Down Sugar Cookies
Step 1: Prep Your Oven and Pans
Start by preheating your oven to 350 degrees. If you have a mini round cake pan, now’s the time to pull it out—this is the secret to that iconic look. No need to fuss with liners, just set it aside while you prepare the magic.
Step 2: Cream Butter and Sugar
In a large mixing bowl, add your room temperature butter and granulated sugar together. Beat them until the mixture turns pale and fluffy—think of this as injecting little air bubbles that will give these Pineapple Upside Down Sugar Cookies their soft, light texture.
Step 3: Mix in Eggs, Vanilla, and Sour Cream
Crack in those eggs, pour in the vanilla, and dollop in the sour cream. Blend until everything is creamy and smooth. Each of these ingredients adds its own magic, making the dough rich and tender.
Step 4: Combine Dry Ingredients
Sprinkle your flour, baking powder, cornstarch, and salt into a separate bowl, then gently mix them into the wet ingredients. Stir just until a dough forms—overmixing can make cookies tough, and we’re all about that soft bite!
Step 5: Make the Caramel Base
In a medium bowl, whisk together the melted butter and packed light brown sugar. This duo creates the gooey, caramel-like bottom (which, as you’ll see later, is actually the top) that sets Pineapple Upside Down Sugar Cookies apart.
Step 6: Assemble Cookie Bases
Spoon about a tablespoon of the brown sugar-butter mixture into each well of your mini round cake pan, spreading it to cover the bottom. This forms the sticky sweet treat that makes these cookies oh-so-special.
Step 7: Add Pineapple and Cherry
Next, carefully set a pineapple ring on top of the brown sugar base, and nestle a maraschino cherry right in the middle. The colors and aromas scream “vacation in a bite!”
Step 8: Top with Sugar Cookie Dough
Use a three-tablespoon cookie scoop to create even mounds of dough (if you don’t have one, a little over two tablespoons will do), then gently press and flatten the dough over the pineapple and cherry using an offset spatula or the back of a spoon. Be sure to fully cover the fruit so all that caramel goodness gets trapped inside.
Step 9: Bake to Golden Perfection
Slide your pan into the oven and bake for 25 minutes, or until the edges are golden and you can hear or see those delightful brown sugar bubbles. Resist the urge to peek too early—the anticipation is part of the fun!
Step 10: Cool and Flip
Let the cookies cool in the pan about 10 minutes, then carefully invert them onto a sheet of wax paper. A bit of brown sugar may ooze out (delicious!), so wax paper keeps things mess-free. If any pineapple sticks, just reposition it atop the cookie.
Step 11: Enjoy When Cool
Let the Pineapple Upside Down Sugar Cookies cool completely before serving, so every bite is the perfect blend of chewy, gooey, and vibrant. Store the leftovers airtight, but trust me—these cookies rarely stick around for long!
How to Serve Pineapple Upside Down Sugar Cookies
Garnishes
Turn your Pineapple Upside Down Sugar Cookies into showstoppers with a simple dusting of powdered sugar, a small dollop of whipped cream, or an extra cherry on top. For a tropical flair, sprinkle on some shredded coconut or a zest of lime—just a little goes a long way and makes each cookie look extra-celebratory.
Side Dishes
Pair these cookies with bowls of fresh fruit salad, tangy Greek yogurt, or creamy vanilla ice cream to complement their rich, fruity flavor. If you’re brewing coffee or tea, serve these on the side—they’re excellent for dunking!
Creative Ways to Present
Stack Pineapple Upside Down Sugar Cookies on a tiered dessert stand for parties, or wrap each one individually in cellophane with a colorful ribbon as a sweet gift. Another fun idea: make a cookie sundae by topping a warm cookie with ice cream, pineapple chunks, and an extra drizzle of caramel sauce for a true retro dessert experience.
Make Ahead and Storage
Storing Leftovers
Once cooled, store your Pineapple Upside Down Sugar Cookies in an airtight container on the countertop. They’ll taste best within the first two to three days—after that, the fruit topping may soften the cookies a little, but they’re still delicious.
Freezing
Want to enjoy these treats later? Arrange completely cooled cookies in a single layer in a freezer-safe container, adding parchment or wax paper between layers. They’ll keep in the freezer for up to two months. Thaw at room temperature before serving, and you’ll have a taste of summer ready whenever you crave it.
Reheating
If you like your cookies warm, reheat individual Pineapple Upside Down Sugar Cookies in the microwave for about 10-12 seconds. Just enough to bring back that caramelized topping and soften the cookie slightly—like it’s fresh from the oven!
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Just make sure your fresh pineapple rings are well-drained and patted dry before assembly, as extra juice can make the cookies too moist and cause sticking.
What if I don’t have a mini round cake pan?
No worries! You can use a standard muffin tin instead. The cookies might be a bit thicker, but they’ll have the same signature look and taste—just watch the baking time and adjust as needed.
Can Pineapple Upside Down Sugar Cookies be made gluten-free?
Yes, you can swap the all-purpose flour for your favorite gluten-free 1-to-1 baking flour blend. Just keep an eye on texture; you may need a touch more or less flour depending on the brand.
Why is my brown sugar topping sticking to the pan?
Pineapple juice or too much brown sugar can sometimes stick, especially if the cookies cool too long in the pan. Let them rest for 10 minutes then invert while still slightly warm, and if anything sticks, just use a spoon to help it along and place it back on the cookie.
Can I make these cookies ahead of time?
You can prep the dough and assemble everything a day ahead, then bake right before serving. Alternatively, bake the Pineapple Upside Down Sugar Cookies completely, store airtight, and serve within two days for best texture and flavor.
Final Thoughts
I truly hope you fall head over heels for these Pineapple Upside Down Sugar Cookies! They’re sunny, sweet, and always a conversation starter. If you give them a try, I promise you’ll turn any gathering into a tropical celebration. Happy baking!
Print
Pineapple Upside Down Sugar Cookies Recipe
- Total Time: 45 minutes
- Yield: 13 cookies 1x
- Diet: Vegetarian
Description
These Pineapple Upside Down Sugar Cookies are a delightful twist on the classic dessert. Buttery sugar cookie dough is topped with sweet caramelized brown sugar, juicy pineapple slices, and bright maraschino cherries for a taste of tropical paradise in every bite.
Ingredients
Cookies:
- 1 cup butter (room temperature)
- 1 1/2 cups granulated sugar
- 2 eggs
- 2 tsp. vanilla extract
- 1/2 cup sour cream
- 3 cups all-purpose flour
- 1 tsp. baking powder
- 1 tsp. cornstarch
- 1/2 tsp. salt
Topping:
- 13 canned pineapple slices
- 13 maraschino cherries
- 1/2 cup butter (melted)
- 1 cup light brown sugar (packed)
Instructions
- Preheat oven to 350 degrees. Prepare mini round cake pan.
- Cream butter and sugar: Beat butter and sugar until light and fluffy.
- Add eggs and flavorings: Mix in eggs, vanilla, and sour cream.
- Combine dry ingredients: Add flour, baking powder, cornstarch, and salt; mix until combined.
- Prepare topping: Combine melted butter and brown sugar.
- Assemble cookies: Add brown sugar mixture to each cavity, top with pineapple slice and cherry, then cookie dough.
- Bake: Bake for 25 minutes until golden and bubbly.
- Cool and serve: Let cool, invert onto wax paper, cool completely before serving.
Notes
- For best results, ensure ingredients are at room temperature.
- Use wax paper to prevent sticking when cooling cookies.
- Store cookies in an airtight container for freshness.
- Prep Time: 20 minutes
- Cook Time: 25 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 280
- Sugar: 20g
- Sodium: 180mg
- Fat: 12g
- Saturated Fat: 7g
- Unsaturated Fat: 4g
- Trans Fat: 0g
- Carbohydrates: 40g
- Fiber: 1g
- Protein: 3g
- Cholesterol: 50mg
Keywords: Pineapple, Upside Down, Sugar Cookies, Dessert, Baking, Tropical
