Pineapple Upside Down Sugar Cookies Recipe

These Pineapple Upside Down Sugar Cookies transform the classic cake into adorable, individual-sized treats that are bursting with caramelized sweetness! Featuring buttery sugar cookies topped with gooey brown sugar, juicy pineapple rings, and bright maraschino cherries, these cookies deliver all the nostalgic flavors of the traditional dessert in a fun, handheld format. Perfect for parties, potlucks, or whenever you want to bring a smile to someone’s face!

Why You’ll Love This Recipe

• Best of Both Worlds: Combines the beloved flavors of pineapple upside down cake with the convenience and charm of a soft sugar cookie.
• Individual Servings: Each cookie is its own mini upside-down cake, making them perfect for sharing and portion control.
• Impressive Presentation: These cookies look absolutely stunning with their caramelized pineapple rings and cherries, yet they’re surprisingly simple to make.
• Make-Ahead Friendly: You can prepare components ahead of time and assemble when ready to bake.

this Recipe

Ingredients You’ll Need

• Butter: Used in both the cookie dough and caramel mixture, creating richness and that signature buttery flavor. Make sure it’s room temperature for the cookie dough for proper creaming.
• Granulated Sugar: Sweetens the cookie dough and helps create that tender, soft texture we love in sugar cookies.
• Eggs: Provide structure and help bind all the ingredients together. They also add richness to the cookie base.
• Vanilla Extract: Adds that warm, aromatic flavor that enhances all the other ingredients. Don’t skimp here!
• Sour Cream: The secret weapon for incredibly soft, tender cookies that stay moist for days. It adds a subtle tang that balances the sweetness perfectly.
• All-Purpose Flour: Forms the structure of our cookies. Measure correctly by spooning into measuring cups and leveling off for best results.
• Baking Powder: Provides just the right amount of lift to keep these cookies from being too dense.
• Cornstarch: A baker’s trick for extra soft cookies with a melt-in-your-mouth texture.
• Salt: Balances the sweetness and enhances all the flavors. Don’t skip it!
• Canned Pineapple Slices: The star of the show! They caramelize beautifully with the brown sugar for that classic flavor.
• Maraschino Cherries: Not just for decoration—they add a pop of color and that signature sweet cherry flavor.
• Brown Sugar: Creates that irresistible caramel-like topping that makes pineapple upside down desserts so special.

Variations

Different Fruit Combinations

Try replacing the pineapple with other fruits like peach slices or apple rings for a seasonal twist. You can also add blueberries around the cherry for a patriotic look during summer holidays.

Flavor Additions

Add a teaspoon of cinnamon to the cookie dough for a warm spice note, or try a splash of rum extract in the brown sugar mixture for a tropical flavor boost.

Mini or Maxi

Make bite-sized versions using mini muffin pans and pineapple tidbits, or create one giant cookie in a cast iron skillet for a shareable dessert.

Coconut Lover’s Version

Sprinkle some shredded coconut onto the brown sugar mixture before adding the pineapple for a tropical twist that adds wonderful texture.

How to Make Pineapple Upside Down Sugar Cookies

Step 1: Prepare Your Equipment and Ingredients

Preheat your oven to 350°F. Set aside a mini round cake pan. Drain your pineapple slices and pat them dry with paper towels to prevent excess moisture in your cookies.

Step 2: Make the Cookie Dough

In a large mixing bowl, cream together the room temperature butter and granulated sugar until light and fluffy, about 3 minutes. This step is crucial for a tender cookie, so don’t rush it! Add the eggs, vanilla extract, and sour cream, mixing until well combined. The mixture might look a bit curdled, but that’s perfectly normal.

Step 3: Add Dry Ingredients

Gradually add the flour, baking powder, cornstarch, and salt to the wet ingredients. Mix just until the dough comes together – overmixing will make your cookies tough. The dough will be soft and slightly sticky.

Step 4: Prepare the Brown Sugar Mixture

In a separate bowl, combine melted butter and brown sugar, stirring until smooth and well-incorporated. This simple mixture will transform into the magical caramelized topping that makes these cookies irresistible.

Step 5: Assemble the Cookies

Add about a tablespoon of the brown sugar mixture to the bottom of each cavity in your pan, spreading it evenly. Place a pineapple slice on top of the brown sugar layer, then nestle a maraschino cherry in the center of each pineapple ring.

Step 6: Add Cookie Dough

Scoop approximately 3 tablespoons of cookie dough on top of each pineapple slice. Using an offset spatula, gently flatten the dough to cover the pineapple. Don’t worry about making it perfect – it will spread as it bakes.

Step 7: Bake to Golden Perfection

Bake for 25 minutes, or until the edges are golden brown and you can see the brown sugar mixture bubbling up around the sides. Your kitchen will smell amazing!

Step 8: Cool and Flip

Allow the cookies to cool in the pan for exactly 10 minutes – not too short, not too long. This timing is crucial for proper release! Then carefully invert the pan onto a wax paper-covered surface. The brown sugar caramel will be hot and runny, so the wax paper is essential.

Pro Tips for Making the Recipe

• Room Temperature Ingredients: Make sure your butter, eggs, and sour cream are at room temperature for the best texture and even mixing.
• Don’t Overbake: These cookies are best when slightly soft in the center, so remove them from the oven when the edges are golden but the centers still look slightly underdone.
• Perfect Timing for Flipping: The 10-minute cooling period is crucial – too soon and they’ll fall apart, too late and the caramel will harden, making them stick to the pan.
• Pineapple Preparation: Pat your pineapple slices dry before using them to prevent excess moisture that can make your cookies soggy.
• Even Distribution: Make sure your brown sugar mixture covers the entire bottom of each cavity for that perfect caramelized effect.

How to Serve

Perfect Pairings

These cookies are wonderful served slightly warm with a scoop of vanilla ice cream on the side. The contrast between the warm cookie and cold ice cream is simply divine!

Dress Them Up

For special occasions, dust the cookies with a little powdered sugar or drizzle with a simple vanilla glaze for extra sweetness and visual appeal.

Coffee Shop Style

Serve alongside a cup of freshly brewed coffee or a latte – the slight bitterness of coffee perfectly complements the sweet caramelized flavors in these cookies.

Make Ahead and Storage

Storing Leftovers

Store completely cooled cookies in an airtight container at room temperature. Place pieces of parchment paper between layers to prevent sticking. These cookies are best enjoyed within 2-3 days while the texture is still perfect.

Freezing

You can freeze the unbaked cookie dough for up to 3 months. When ready to use, thaw in the refrigerator overnight before assembling and baking. Fully baked cookies can also be frozen, but the texture of the pineapple and caramel may change slightly upon thawing.

Reheating

To refresh day-old cookies, warm them in the microwave for 10-15 seconds. This reactivates the gooey caramel and makes them taste nearly fresh-baked!

FAQs

Can I use fresh pineapple instead of canned?
While fresh pineapple has wonderful flavor, canned pineapple actually works better in this recipe. Fresh pineapple contains enzymes that can break down proteins in the dough, potentially affecting the texture. If you do use fresh, blanch it briefly in boiling water first to neutralize these enzymes.

My cookies stuck to the pan when I tried to flip them. What went wrong?
Timing is everything with upside down desserts! Make sure to let them cool exactly 10 minutes before flipping. Also, ensure you’ve used enough of the butter-brown sugar mixture on the bottom. If a pineapple slice sticks, simply place it back on top of the cookie – no one will know!

Can I make these without a special mini cake pan?
Absolutely! A standard muffin tin works well for slightly smaller cookies. You’ll need to reduce the baking time by about 5 minutes and use pineapple tidbits or rings cut to fit. Alternatively, you could make one large version in a 9-inch cake pan, increasing the baking time to about 35-40 minutes.

The brown sugar mixture hardened before I could flip my cookies. Can they be saved?
If this happens, place the pan back in the warm (but turned off) oven for about 2 minutes to soften the caramel, then try flipping again. In the future, make sure to flip while the caramel is still warm but the cookies have had enough time to set.

Final Thoughts

These Pineapple Upside Down Sugar Cookies are a delightful twist on two beloved desserts. They capture all the nostalgic flavors of the classic cake while offering the convenience and charm of cookies. Whether you’re making them for a family dessert, bringing them to a potluck, or gifting to friends, they’re sure to bring smiles and requests for the recipe. The combination of buttery cookie, caramelized brown sugar, juicy pineapple, and sweet cherry creates a perfect bite that’s truly irresistible. Give them a try – I promise they’ll become a new favorite in your baking repertoire!

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