Pineapple Upside Down Sugar Cookies

These Pineapple Upside Down Sugar Cookies transform a classic cake into handheld treats perfect for summer gatherings. Each cookie features a soft, fluffy sugar cookie base topped with caramelized brown sugar, juicy pineapple, and a bright maraschino cherry. They deliver all the nostalgic flavor of the traditional cake in a convenient, portable form.

I brought these to our neighborhood block party last weekend, and they disappeared within minutes! My neighbor, who claims to be a pineapple upside down cake purist, admitted these cookies might actually be better than the original. The individual portions make serving easy, and everyone loved having their own personal treat without needing plates or forks.

Ingredients With Purpose

• Butter: creates a rich, tender cookie base; room temperature ensures proper creaming with sugar
• Sour cream: adds moisture and tanginess that balances the sweetness; creates an exceptionally soft texture
• Cornstarch: the secret to keeping these cookies tender and preventing them from spreading too much
• Canned pineapple slices: provide perfect portion-sized fruit that holds its shape during baking
• Maraschino cherries: add a pop of color and sweet-tart flavor that complements the pineapple
• Brown sugar: caramelizes during baking to create that signature sticky-sweet glaze
• Vanilla extract: enhances all the flavors and adds depth to the simple sugar cookie base

Pin it

Detailed Cooking Instructions

Step 1:

Begin by preheating your oven to 350°F (175°C). The moderate temperature allows the cookies to bake evenly while giving the brown sugar time to caramelize without burning. Set aside your mini round cake pan, ensuring it's clean and dry for the best release later.

Step 2:

In a large mixing bowl, combine 1 cup of room temperature butter with 1½ cups of granulated sugar. Beat them together until the mixture becomes noticeably lighter in both color and texture, about 3-4 minutes. This creaming process incorporates air into the dough, which helps create that soft, fluffy texture we're looking for. Don't rush this step - proper creaming is essential for the perfect cookie texture.

Step 3:

Add 2 eggs, 2 teaspoons of vanilla extract, and ½ cup of sour cream to your butter-sugar mixture. Mix until everything is well combined and smooth. The sour cream might look slightly curdled at first, but continue mixing and it will incorporate beautifully, adding moisture and a subtle tang that balances the sweetness.

Step 4:

In a separate bowl, whisk together 3 cups of all-purpose flour, 1 teaspoon of baking powder, 1 teaspoon of cornstarch, and ½ teaspoon of salt. This pre-mixing ensures the leavening agents and salt are evenly distributed throughout the dough. Add this dry mixture to your wet ingredients and mix just until the cookie dough comes together. Overmixing at this stage can develop too much gluten, resulting in tough cookies, so stop mixing as soon as no dry flour remains visible.

Step 5:

For the caramel topping, melt ½ cup of butter in a microwave-safe bowl or small saucepan. Add 1 cup of packed light brown sugar and stir until thoroughly combined. The mixture should be smooth and glossy, with the sugar partially dissolved in the melted butter.

The Magic of Transformation

What makes these cookies truly special is the dramatic transformation they undergo during baking. The brown sugar and butter mixture starts as a simple syrup but emerges from the oven as a complex caramel with notes of toffee and butterscotch. As it bubbles and caramelizes, it infuses the pineapple with its rich flavor while creating that signature sticky-sweet glaze that defines a great pineapple upside down dessert.

I've found that allowing the cookies to cool in the pan for exactly 10 minutes creates the perfect balance - long enough for the caramel to set slightly so it doesn't all run off, but not so long that it hardens and sticks permanently to the pan. That moment of flipping the pan and revealing the glistening pineapple tops never fails to bring a smile, no matter how many times I've made these cookies.

The contrast between the warm, caramelized fruit topping and the soft, vanilla-scented cookie base creates a multi-dimensional treat that satisfies on so many levels. Each bite offers the perfect balance of flavors and textures - sweet, buttery, fruity, and tender all at once.

Pin it

A Nostalgic Twist on Tradition

These cookies capture the essence of summer gatherings and family traditions while putting a fresh spin on a classic dessert. Pineapple upside down cake has been gracing American tables since the 1920s when the Hawaiian Pineapple Company (now Dole) started promoting recipes featuring their canned pineapple. This cookie version honors that heritage while making it more accessible for modern, on-the-go lifestyles.

I've served these at everything from backyard barbecues to elegant brunch gatherings, and they always feel appropriate. There's something about the combination of caramelized pineapple and cherries that evokes a sense of nostalgic comfort while still feeling special. The individual portions make them perfect for serving at events where people might be mingling rather than sitting down for a formal dessert course.

For an extra special presentation, I sometimes add a small dollop of lightly sweetened whipped cream beside each cookie when serving them as a plated dessert. The cool creaminess provides a wonderful contrast to the warm, sticky cookies and elevates them to restaurant-quality status with minimal effort.

I once made these for a summer potluck and forgot the wax paper when flipping them out. The caramel ended up all over my countertop, creating quite the sticky situation! Now I always prepare my turning surface before the cookies even go into the oven, ensuring a smooth (if still slightly messy) process.

The first time I made these cookies, I was skeptical about whether the sugar cookie base would hold up to the moisture of the fruit and caramel. I was pleasantly surprised to find that the cookie not only maintained its structure but actually absorbed some of the caramel flavor, creating an even more delicious treat than I had anticipated.

These Pineapple Upside Down Sugar Cookies have become one of my signature summer desserts, requested at gatherings and perfect for satisfying my topping-loving tendencies. The individual portions ensure everyone gets their fair share of that irresistible caramelized pineapple and cherry topping, eliminating the need to sneakily pick off all the good parts like I might do with a traditional cake!

Frequently Asked Questions

→ Can I use fresh pineapple instead of canned?

Fresh pineapple isn't recommended for this recipe as it contains enzymes that can break down the cookie dough. Canned pineapple has been processed in a way that deactivates these enzymes.

→ What pan should I use for these cookies?

The recipe calls for a mini round cake pan. If you don't have one, you could use a muffin tin, though the cookies will be smaller.

→ How do I store these cookies?

Store them in an airtight container at room temperature. They're best eaten within 2-3 days of baking.

→ Can I freeze these cookies?

Yes, you can freeze them in an airtight container with parchment paper between layers for up to 3 months. Thaw at room temperature before serving.

→ What if my pineapple sticks to the pan when flipping?

As mentioned in the recipe, if the pineapple sticks to the pan, simply reposition it back on top of the cookie after flipping.