Pineapple Upside Sugar Cookies

This pineapple upside-down sugar cookie recipe transforms a classic cake into handheld treats that bring tropical flavor to your dessert table. The combination of buttery cookie base with caramelized pineapple and cherries creates an irresistible treat that looks as impressive as it tastes.

I first made these cookies for a summer potluck when I wanted something more exciting than standard cookies. The moment I flipped them over and revealed those glossy pineapple rings, everyone at the party crowded around asking for the recipe.

Ingredients

• Butter: at room temperature creates a tender cookie base and rich flavor
• Granulated sugar: provides the perfect level of sweetness for the dough
• Large eggs: bind everything together while adding moisture
• Vanilla extract: enhances all the flavors in the cookie
• Sour cream: is the secret ingredient that makes these cookies exceptionally soft
• All purpose flour: provides structure for the cookie dough
• Baking powder: ensures the cookies rise properly
• Cornstarch: creates that melt in your mouth texture we all love
• Salt: balances the sweetness and enhances flavor

• Canned pineapple slices: work perfectly here look for ones packed in juice rather than syrup for best flavor
• Maraschino cherries: add that classic pop of color and sweet flavor
• Melted butter: combines with brown sugar to create the caramelized base
• Light brown sugar: packed creates that signature caramel flavor that makes this dessert special

Step-by-Step Instructions

Prepare Your Equipment:

Preheat your oven to 350°F and prepare your mini round cake pan or muffin tin. I recommend a light spritz of cooking spray even though the butter mixture will help prevent sticking. The brown sugar mixture can become quite sticky once baked.

Create The Cookie Base:

In a large bowl cream together the room temperature butter and granulated sugar until the mixture becomes noticeably lighter in color and fluffy in texture. This should take about 3 minutes with an electric mixer. The air incorporated during this step is crucial for a soft texture.

Add Wet Ingredients:

Add the eggs one at a time mixing well after each addition then add the vanilla extract and sour cream. Mix until completely combined scraping down the sides of the bowl to ensure everything is evenly incorporated. The mixture might look slightly curdled this is normal.

Combine Dry Ingredients:

In a separate bowl whisk together the flour baking powder cornstarch and salt. Mixing these separately ensures they will be evenly distributed throughout the dough preventing any pockets of salt or baking powder.

Form The Dough:

Gradually add the dry ingredients to the wet mixture mixing on low speed until just combined. Do not overmix or your cookies will become tough. The dough should be soft but not sticky enough to easily handle with your hands or a scoop.

Create The Caramel Base:

In another bowl stir together the melted butter and brown sugar until completely smooth. This mixture will caramelize in the oven creating that signature sticky sweet topping that makes upside down desserts so delicious.

Assemble The Cookies:

Add about 1 tablespoon of the brown sugar mixture to the bottom of each cavity spreading it evenly. Place a pineapple slice on top of the sugar mixture then add a maraschino cherry in the center of each pineapple ring creating that classic upside down cake look.

Add Cookie Dough:

Using a 3 tablespoon scoop add cookie dough on top of each pineapple slice gently pressing down with an offset spatula to create an even layer. Make sure the dough reaches the edges to seal in the topping.

Bake To 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 fill with an amazing caramel pineapple aroma when they are nearly done.

Cool And Flip:

Let the cookies cool in the pan for exactly 10 minutes. This cooling time is crucial too short and the topping will be too runny too long and it might stick to the pan. Place a sheet of wax paper on a cooling rack then carefully flip the pan over to release the cookies.

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The first time I made these cookies I used fresh pineapple which was a disaster the extra moisture made the caramel too runny. Stick with canned pineapple rings which have a consistent moisture level and are already perfectly shaped for these cookies.

Storage Tips

These cookies are at their absolute best the day they're made but will keep well in an airtight container at room temperature for 2-3 days. Place pieces of parchment paper between layers to prevent sticking. For longer storage you can refrigerate them for up to a week but bring to room temperature before serving for the best texture.

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Serving Suggestions

For an extra special dessert serve these cookies slightly warm with a scoop of vanilla ice cream on the side. The contrast of warm cookie and cold ice cream is heavenly. You can also drizzle a bit of extra caramel sauce over the top for an even more decadent treat. These cookies make a beautiful presentation on a dessert table when arranged on a cake stand.

Making Ahead

You can prepare the cookie dough up to 2 days in advance and refrigerate it just bring it to room temperature before using. The assembled unbaked cookies can be prepared a few hours ahead and held in the refrigerator until ready to bake just add a few extra minutes to the baking time if they're cold when they go in the oven.

Recipe FAQs

→ Can I use fresh pineapple instead of canned?

Yes, you can use fresh pineapple, but ensure you cut it into thin, consistent slices for even caramelization.

→ How do I prevent the topping from sticking to the pan?

Grease the pan well, and invert the cookies onto wax paper while warm to release the topping easily.

→ Can I make these cookies dairy-free?

Yes, substitute the butter and sour cream with non-dairy alternatives for a dairy-free version.

→ What is the best way to store these cookies?

Store the cookies in an airtight container for up to 2–3 days to maintain freshness and prevent drying out.

→ Can I make smaller portions using smaller pans?

Yes, you can use muffin tins to create smaller cookies, adjusting the topping and dough portions accordingly.