Introduction

Pineapple Upside Down Sugar Cookies are a delightful twist on the classic pineapple upside down cake. These individual cookies feature a caramelized pineapple slice and cherry on the bottom, creating a sweet and tangy topping once flipped. Perfect for a fun dessert or special treat, they are sure to impress both family and friends.

The image shows four small round pineapple upside-down cakes placed on a white marbled surface. Each cake has a thick, golden-brown base layer with a rough, moist texture. On top of this base, there is a bright yellow pineapple ring with a shiny glaze, making it look juicy and fresh. At the center of every pineapple ring is a small, vivid red cherry, adding a pop of color and glossy texture. The cakes have a slightly sticky syrup around the base, creating a glistening effect. The overall look is warm and inviting, with the cakes spaced evenly. photo taken with an iphone --ar 4:5 --v 7

Ingredients

1 cup butter (room temperature)
1 1/2 cups granulated sugar
2 eggs
2 tsp. vanilla extract
1/2 cup sour cream
3 cups all-purpose flour
1 tsp. baking powder
1 tsp. cornstarch
1/2 tsp. salt
13 canned pineapple slices
13 maraschino cherries
1/2 cup butter (melted)
1 cup light brown sugar (packed)

Instructions

Step 1: Preheat your oven to 350 degrees F and prepare a USA pan mini round cake pan.
Step 2: In a large bowl, cream together the room temperature butter and granulated sugar until the mixture is light and fluffy.
Step 3: Add the eggs, vanilla extract, and sour cream, mixing until fully combined.
Step 4: In a separate bowl, whisk together the flour, baking powder, cornstarch, and salt. Gradually add to the wet ingredients and mix just until the dough comes together. Set aside.
Step 5: In another bowl, combine the melted butter and light brown sugar, stirring until smooth.
Step 6: Spoon about one tablespoon of the brown sugar mixture into the bottom of each cavity of the baking pan, spreading it evenly to cover.
Step 7: Place one pineapple slice on top of the brown sugar in each cavity, then press a maraschino cherry into the center of each pineapple slice.
Step 8: Using a 3-tablespoon cookie scoop, drop cookie dough onto the pineapple topping. Flatten the dough gently with an offset spatula to cover evenly.
Step 9: Bake for about 25 minutes, or until cookie edges turn golden brown and the brown sugar mixture bubbles up the sides.
Step 10: Allow the cookies to cool for 10 minutes, then carefully invert the pan onto a wax paper-lined surface. Be ready for some brown sugar to run. If any pineapple sticks to the pan, reposition it onto the cookie.
Step 11: Let the cookies cool completely before serving. Store any leftovers in an airtight container.

Tips & Variations

Use fresh pineapple slices if preferred; just pat them dry to avoid soggy cookies.
Try adding a pinch of cinnamon or nutmeg to the dough for a warm spice flavor.
For a dairy-free version, substitute butter and sour cream with plant-based alternatives.
Line the pan with parchment for easier cleanup and release.

Storage

Store the cooled cookies in an airtight container at room temperature for up to 3 days to maintain freshness. To reheat, warm in a low oven or microwave briefly to restore softness and bring out the caramel flavors.

How to Serve

Six small round pineapple upside-down mini cakes are arranged on a white plate with a white marbled texture background. Each cake has three clear layers: the bottom layer is golden brown with a slightly crispy textured edge, the middle layer is a moist yellow cake, and the top layer is a shiny yellow pineapple ring with a bright red cherry placed in the center of the ring. A light amber glaze is drizzled over and around the cakes, creating small drops on the plate. photo taken with an iphone --ar 4:5 --v 7

Serve this delicious recipe with your favorite sides.

FAQs

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple can be used, but make sure to pat the slices dry to prevent excess moisture from affecting the cookie texture.

Why does the brown sugar run when I invert the cookies?

The melted brown sugar and butter mixture caramelizes and becomes syrupy during baking, so when flipped, it naturally runs. Lining your work surface with wax paper helps contain the sticky sweetness and makes cleanup easier.