If you adore the tropical sweetness of pineapple combined with the comforting charm of sugar cookies, you’re in for a real treat with this Pineapple Upside Down Sugar Cookies Recipe. These cookies take the classic pineapple upside down cake idea and transform it into a handheld delight that’s bursting with buttery, caramelized brown sugar goodness under a soft, fluffy cookie. Imagine biting into a golden cookie that reveals a juicy pineapple slice and a vibrant cherry at its core, creating the perfect harmony of fruity freshness and cookie warmth. This recipe is not just delicious, it’s also a fun twist on two beloved desserts that will have your friends and family asking for seconds every time.
Ingredients You’ll Need
What’s fantastic about this Pineapple Upside Down Sugar Cookies Recipe is how it combines pantry staples with a few special touches to create those irresistible flavors and textures. Each ingredient is thoughtfully chosen to blend richness, sweetness, and that familiar tropical zing perfectly.
- Butter (1 cup, room temperature): The base of both the cookie dough and the luscious brown sugar glaze, giving moisture and richness.
- Granulated sugar (1 ½ cups): Adds sweetness and helps create that perfectly tender cookie crumb.
- Eggs (2): Bind everything together and contribute to the cookie’s fluffy texture.
- Vanilla extract (2 teaspoons): Lends a warm, aromatic depth that complements the tropical fruit beautifully.
- Sour cream (½ cup): Keeps the cookies moist and tender with just the right tang.
- All-purpose flour (3 cups): Provides structure without weighing the cookies down.
- Baking powder (1 teaspoon): A gentle leavening agent that helps the cookies rise just enough.
- Cornstarch (1 teaspoon): Adds softness by tenderizing the flour proteins.
- Salt (½ teaspoon): Balances sweetness and enhances all other flavors.
- Canned pineapple slices (13): The star of the show, offering juicy tropical flavor and a gorgeous presentation.
- Maraschino cherries (13): Bright, sweet centers that bring a pop of color and an extra hint of sugary goodness.
- Melted butter (½ cup): Mixed with brown sugar to form the irresistible caramel-like glaze at the cookie base.
- Light brown sugar (1 cup, packed): Adds deep molasses notes essential for that classic pineapple upside down flavor.
How to Make Pineapple Upside Down Sugar Cookies Recipe
Step 1: Preheat the Oven and Prep the Pan
Start by cranking your oven up to 350°F, ensuring it reaches the perfect temperature by the time your dough is ready. Grab a mini round cake pan or a similarly shaped pan designed to hold individual cookies and set it aside. This pan is crucial because it shapes the cookie so that your pineapple slice and cherry sit perfectly at the bottom, where the magic happens.
Step 2: Mix the Cookie Dough
In a large bowl, cream together the butter and granulated sugar until the mixture looks light and fluffy — this step is where much of the cookie’s texture and tenderness begins. Then, add in your eggs, vanilla extract, and sour cream, mixing thoroughly. The sour cream is the secret ingredient here, keeping your cookies wonderfully moist. Next up, sift in the flour, baking powder, cornstarch, and salt. Fold these dry ingredients gently until the dough just comes together, ensuring you don’t overmix which can toughen the cookie.
Step 3: Prepare the Brown Sugar Glaze
In a separate bowl, whisk together the melted butter and the packed light brown sugar until smooth and combined. This sweet, buttery glaze is what caramelizes beautifully in the oven, giving those cookies their signature sticky, golden base reminiscent of classic pineapple upside down cake.
Step 4: Assemble the Cookies
Drop about one tablespoon of the brown sugar glaze into the bottom of each cavity in your prepared pan. Gently place one pineapple slice on top of each tablespoon of glaze, then nestle a maraschino cherry right in the pineapple’s center. Finally, carefully scoop roughly three tablespoons of cookie dough on top of the pineapple slice, flattening it slightly so it bakes evenly. This assembly guarantees that each cookie will have that gorgeous decorative slice of pineapple on the bottom once flipped.
Step 5: Bake and Cool
Pop your assembled cookies into the oven and bake for about 25 minutes. You’ll know they’re ready when the edges turn a light golden brown and the brown sugar glaze bubbles invitingly around the edges. Allow the cookies to cool in the pan for 10 minutes to set the glaze, then carefully turn them out onto wax paper. If the pineapple shifts during flipping, just nudge it back into place. Let the cookies cool completely before serving to ensure the glaze solidifies into that perfect sticky finish.
How to Serve Pineapple Upside Down Sugar Cookies Recipe
Garnishes
These cookies look stunning on their own but adding a few extra touches can really elevate their presentation. A light dusting of powdered sugar adds delicate sweetness and visual appeal. You might also drizzle a bit of honey or a thin glaze over the top for shine and extra flavor contrast. Fresh mint leaves can add a pop of color and a refreshing hint that pairs nicely with the fruity notes.
Side Dishes
These cookies are a lovely standalone treat, but pairing them with certain sides makes for a delightful dessert spread. Fresh whipped cream or a scoop of vanilla bean ice cream complements the warm, buttery flavors perfectly. A cup of chilled coconut milk on the side can highlight the tropical vibes, or serve with a cup of herbal tea to balance sweetness with a gentle, earthy palate.
Creative Ways to Present
Try serving these Pineapple Upside Down Sugar Cookies Recipe on a decorative platter lined with banana leaves or tropical floral accents for an island-inspired vibe. You could even stack them like mini cakes, layering the cookies with cream cheese frosting or pineapple jam between for a whimsical dessert. For parties, place each cookie in a colorful cupcake liner to make grabbing one a breeze while showing off those gorgeous pineapple and cherry centers.
Make Ahead and Storage
Storing Leftovers
Store any leftovers in an airtight container at room temperature to maintain their soft texture and vibrant flavors. For the best taste and freshness, enjoy within 2 to 3 days. The rich brown sugar glaze helps keep the cookies moist, so they won’t dry out quickly.
Freezing
If you want to make these ahead of time, you can freeze the completely cooled cookies. Place them in a single layer on a baking sheet to flash freeze, then transfer them to a freezer-safe container or bag, separating layers with parchment paper. They keep well for up to 2 months, making them a perfect make-ahead treat for unexpected guests or a sunny afternoon craving.
Reheating
For warm, fresh-baked flavor after freezing or storing, reheat cookies in a 300°F oven for about 5 to 7 minutes. This warms the brown sugar glaze back to its soft, sticky goodness and revives the buttery cookie texture. Avoid microwaving as it can make the cookies chewy or dry.
FAQs
Can I use fresh pineapple instead of canned for the Pineapple Upside Down Sugar Cookies Recipe?
Absolutely! Fresh pineapple slices can add an even fresher and juicier taste. Just be sure to cut them about the same thickness as canned slices and pat them dry to avoid excess moisture that could affect baking.
What type of pan works best for baking these pineapple upside down sugar cookies?
A mini round cake pan or muffin pan with individual cavities works best to keep each cookie neatly shaped with the pineapple and cherry on the bottom. If you don’t have one, you can try a regular muffin pan, but the presentation might differ slightly.
Why is sour cream used in the cookie dough?
Sour cream adds moisture and a slight tang, keeping the cookies soft and tender. It also reacts with baking powder to give the cookies a gentle rise and delicate crumb.
Can I substitute maraschino cherries?
Yes! You can use glacé cherries or even fresh cherries if they’re in season. Just remember fresh cherries will add more juiciness and might affect baking time slightly.
How do I prevent the pineapple from sticking to the pan?
Make sure to grease your pan lightly or use a nonstick baking spray before adding the brown sugar glaze. Also, allow the cookies to cool for about 10 minutes before turning them out to ensure the glaze sets, reducing sticking risks.
Final Thoughts
This Pineapple Upside Down Sugar Cookies Recipe has quickly become one of my all-time favorite ways to enjoy a tropical dessert with a cookie twist. It’s simple to prepare, uses ingredients you likely already have, and results in beautiful, flavorful treats that will brighten up any gathering or afternoon snack time. I can’t wait for you to try it and experience that perfect combination of buttery cookie, caramelized brown sugar, and juicy fruit—it’s truly a bite of paradise!
Print
Pineapple Upside Down Sugar Cookies Recipe
- Prep Time: 15 minutes
- Cook Time: 25 minutes
- Total Time: 40 minutes
- Yield: 13 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
These Pineapple Upside Down Sugar Cookies combine classic pineapple upside-down cake flavors with the fun and convenience of a cookie. Featuring a buttery, soft sugar cookie topped with a caramelized brown sugar glaze, a juicy pineapple slice, and a maraschino cherry, this recipe is perfect for a unique dessert or sweet treat. Baked in a mini round cake pan, they have a delightful golden edge and a rich, tropical flavor that everyone will love.
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 the Oven and Prep the Pan: Preheat your oven to 350°F (175°C). Prepare a USA Pan mini round cake pan by ensuring it is clean and ready for the baking process.
- Mix the Cookie Dough: In a large mixing bowl, cream the room temperature butter and granulated sugar together until the mixture is light and fluffy. Add the eggs one at a time, mixing well after each addition, then stir in the vanilla extract and sour cream until fully incorporated. Gradually add the all-purpose flour, baking powder, cornstarch, and salt, mixing gently until the dough just comes together without overmixing.
- Prepare the Brown Sugar Glaze: In a separate bowl, stir together the melted butter and packed light brown sugar until the mixture is smooth and combined to create a luscious glaze.
- Assemble the Cookies: Drop about 1 tablespoon of the brown sugar glaze into the bottom cavity of each section of the mini round cake pan. Place one pineapple slice on top of the brown sugar in each cavity, and set a maraschino cherry in the center of each pineapple slice. Scoop approximately 3 tablespoons of the cookie dough and drop it gently onto the pineapple slice, flattening the dough slightly to cover the fruit evenly.
- Bake and Cool: Bake the assembled cookies at 350°F for about 25 minutes, or until the edges are golden brown and you see the brown sugar bubbling around the sides, indicating caramelization. Remove from the oven and let the cookies cool in the pan for 10 minutes to set before carefully turning them out onto wax paper. If needed, reposition the pineapple slices to ensure an appealing presentation. Allow the cookies to cool completely before serving.
- Storage Tips: Store the Pineapple Upside Down Sugar Cookies in an airtight container to keep them fresh. For optimal flavor and texture, enjoy them within 2-3 days.
Notes
- Use room temperature butter for easier creaming and better texture.
- Press the cookie dough gently to avoid breaking the pineapple slices.
- If the cookies stick when removing from the pan, allow them to cool longer or lightly grease the pan before assembling.
- These cookies can be made ahead and stored in a sealed container at room temperature.
- For a gluten-free version, substitute all-purpose flour with a gluten-free baking blend.
