If you have a soft spot for nostalgic flavors wrapped in a delightful cookie form, you are absolutely going to love this Pineapple Upside Down Sugar Cookies Recipe. Imagine the tropical sweetness of caramelized pineapple and cherries, all nestled atop a buttery, tender sugar cookie base—yes, it’s just as irresistible as it sounds! This recipe combines the charm of a classic pineapple upside down cake with the convenience and fun of cookies, creating a unique treat that’s perfect for any occasion, from casual snacks to festive celebrations.
Ingredients You’ll Need
The beauty of this recipe lies in its simplicity and the careful selection of ingredients that bring together vibrant flavors and pleasing textures. Each component plays a crucial role whether in sweetness, moisture, or that perfect golden color.
- Butter (1 cup, room temperature): This adds richness and creates a tender crumb in the cookies.
- Granulated sugar (1 ½ cups): Provides sweetness and helps with the cookie’s structure.
- Eggs (2): Bind the ingredients while adding moisture.
- Vanilla extract (2 tsp): Enhances the overall flavor with warm, aromatic notes.
- Sour cream (½ cup): Adds moisture and a subtle tang that balances the sweetness beautifully.
- All-purpose flour (3 cups): Forms the body of the cookies, ensuring structure.
- Baking powder (1 tsp): Gives a gentle lift to keep cookies light.
- Cornstarch (1 tsp): Contributes to a soft, delicate texture.
- Salt (½ tsp): Enhances flavors and balances sweetness.
- Canned pineapple slices (13): The star of the show, providing juicy tropical flavor.
- Maraschino cherries (13): Adds a pop of color and sweet tang.
- Butter (½ cup, melted): Used with brown sugar to create the caramelized topping layer.
- Light brown sugar (1 cup, packed): Brings rich molasses notes for that perfect caramelized base.
How to Make Pineapple Upside Down Sugar Cookies Recipe
Step 1: Prepare the Caramelized Base
Start by mixing the melted butter and light brown sugar together, then spoon about a tablespoon of this mixture into the bottom of each cavity in your cookie pan. Spread it evenly so that when baked, it forms a luscious caramel layer that perfectly complements the pineapple topping.
Step 2: Add the Pineapple and Cherry Toppings
Place one canned pineapple slice on top of the brown sugar mixture in each cavity, centering it carefully. Then, nestle a maraschino cherry right in the middle of each pineapple slice. This classic pairing not only looks charming but will deliver that iconic upside down flavor in every bite.
Step 3: Make the Cookie Dough
In a mixing bowl, cream the room temperature butter with granulated sugar until light and fluffy. Beat in the eggs one at a time, followed by the vanilla extract and sour cream. Whisk together the dry ingredients—flour, baking powder, cornstarch, and salt—then gradually fold them into the wet mixture to form a smooth dough that holds just right.
Step 4: Assemble and Bake
Gently spoon or scoop the dough evenly over each pineapple ring in the pan, covering the caramel and fruit entirely. Bake in a preheated oven at 350°F (175°C) for about 18 to 20 minutes or until the cookies are golden and a toothpick inserted into the cookie portion comes out clean. Once done, let them cool slightly before carefully flipping them over to reveal the glossy pineapple upside down topping.
How to Serve Pineapple Upside Down Sugar Cookies Recipe
Garnishes
For an extra touch of elegance, consider dusting your cookies with a little powdered sugar or piping a dollop of whipped cream on the side. Fresh mint leaves add a refreshing contrast and a vibrantly green pop that complements the tropical vibe beautifully.
Side Dishes
These cookies pair wonderfully with a scoop of vanilla ice cream or a light floral tea, such as jasmine or chamomile. Their balance of sweet and tangy makes them a perfect companion to more subtle beverages and light desserts.
Creative Ways to Present
Try arranging these cookies on a bright platter lined with pineapple leaves and slices for an eye-catching display at parties. Another fun idea is to serve them as part of a tropical dessert board alongside coconut macaroons and passion fruit curd in little bowls.
Make Ahead and Storage
Storing Leftovers
These cookies keep well stored in an airtight container at room temperature for up to 3 days, maintaining their tender texture and rich flavor. Keep them away from heat or humidity to prevent the topping from becoming sticky.
Freezing
You can freeze these cookies, either individually wrapped or in a sealed container. They’ll last for up to 2 months in the freezer. Thaw at room temperature before serving for the best texture experience.
Reheating
Warm leftover cookies briefly in a low oven (about 300°F or 150°C) for 5 to 7 minutes or microwave gently to bring back their fresh-baked softness and make that caramelized pineapple topping delightfully warm again.
FAQs
Can I use fresh pineapple instead of canned for this recipe?
Fresh pineapple can be used, but canned pineapple slices are preferred for their uniform size, sweetness, and moisture level. If using fresh, be sure to slice them evenly, and consider lightly caramelizing them in a pan beforehand to mimic the canned texture and flavor.
Do I have to flip the cookies after baking?
Yes, flipping the cookies is essential to reveal the delicious pineapple upside down topping. Let them cool slightly before flipping to avoid breaking or sticking.
Can I make these cookies gluten-free?
Absolutely! Substitute the all-purpose flour with a gluten-free flour blend that can be used cup-for-cup. You may want to add a bit more cornstarch or a binding agent like xanthan gum to improve texture.
Is it okay to use light brown sugar instead of dark brown sugar?
Yes, light brown sugar works perfectly here and will produce a slightly milder caramel flavor, which complements the pineapple beautifully.
How do I prevent the cookies from sticking to the pan?
Make sure to grease your pan well or use a non-stick spray before adding the brown sugar mixture to help release the cookies easily after baking and flipping.
Final Thoughts
Now that you’ve got the full scoop on this charming Pineapple Upside Down Sugar Cookies Recipe, it’s time to roll up your sleeves and make some magic happen in your kitchen. These cookies aren’t just a treat—they’re a delightful conversation starter and a heartwarming way to share a little sunshine with friends and family. Happy baking and enjoy every sweet bite of this tropical classic reinvented!
Print
Pineapple Upside Down Sugar Cookies Recipe
- Prep Time: 20 minutes
- Cook Time: 22 minutes
- Total Time: 42 minutes
- Yield: 13 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
These Pineapple Upside Down Sugar Cookies combine the classic flavors of pineapple upside-down cake with the simplicity and convenience of sugar cookies. Each cookie features a soft, buttery dough topped with a caramelized brown sugar base, a sweet pineapple slice, and a maraschino cherry, baked to golden perfection for a delightful tropical treat.
Ingredients
Cookie Dough
- 1 cup butter, room temperature
- 1 ½ cups granulated sugar
- 2 eggs
- 2 tsp vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 tsp baking powder
- 1 tsp cornstarch
- ½ tsp salt
Topping
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ cup butter, melted
- 1 cup light brown sugar, packed
Instructions
- Prepare the brown sugar topping: In a bowl, mix the melted butter and the packed light brown sugar until well combined. This mixture will create the caramelized base for your cookies.
- Fill the pan cavities: Spoon about 1 tablespoon of the brown sugar mixture into the bottom of each cavity of a prepared muffin or cookie pan. Spread it evenly covering the bottom completely to ensure a sticky, caramelized base.
- Add pineapple and cherries: Place one canned pineapple slice on top of the brown sugar mixture in each cavity, then center a maraschino cherry in the middle of each pineapple slice. This forms the classic upside-down cookie topping.
- Make the cookie dough: In a large mixing bowl, cream together the room temperature butter and granulated sugar until light and fluffy. Beat in the eggs one at a time, followed by vanilla extract and sour cream until well combined.
- Combine dry ingredients and mix: In a separate bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until just combined to form a soft dough.
- Assemble and bake: Drop or spoon the cookie dough evenly over the pineapple and cherry topping in each cavity, covering them completely. Bake in a preheated oven at 350°F (175°C) for 18-22 minutes or until the edges are golden and a toothpick inserted in the dough comes out clean.
- Cool and invert: Allow the cookies to cool in the pan for about 5 minutes. Then carefully invert the pan onto a wire rack or serving dish so the pineapple and cherries become the top of the cookie. Let them cool completely before serving.
Notes
- Use a non-stick muffin tin or grease your pan well to prevent sticking when inverting the cookies.
- You can substitute fresh pineapple slices if preferred; just drain them well.
- For a softer cookie, avoid overbaking; check for doneness at 18 minutes.
- Store cookies in an airtight container at room temperature for up to 3 days.
- For added flavor, sprinkle a pinch of cinnamon in the brown sugar mixture before assembling.
