Description

Nothing can beat the tropical and nostalgic taste of pineapple upside-down desserts Today we’re bringing the deliciousness in miniature cookie form! These Mini Pineapple Upside-Down Cookies are a delicious combination of sweet caramelized pineapple and sweet maraschino cherries as well as a soft, cinnamon-spiced dough base.

Ideal for tea time, parties or as a treat for yourself This easy pineapple-based recipe will bring tropical flavor in your kitchen!

Ingredients

Scale

Dry Ingredients

1 1/4 cups all-purpose flour
1/2 teaspoon baking powder
1/4 teaspoon salt
1/2 teaspoon cinnamon

Wet Ingredients

1/2 cup unsalted butter, softened
3/4 cup brown sugar, packed
1 egg
1 teaspoon vanilla extract

Toppings & Mix-Ins

1/2 cup crushed pineapple, drained
12 maraschino cherries, halved
1/4 cup caramel sauce

Instructions

Step 1: Preheat & Prepare

Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper for easy cleanup.

Step 2: Cream Butter & Sugar

In a large bowl, cream together the butter and brown sugar until light and fluffy. This step is crucial for soft cookies!

Step 3: Add Egg & Vanilla

Beat in the egg and vanilla extract until fully combined. This helps create a smooth and rich dough.

Step 4: Mix Dry Ingredients

In a separate bowl, whisk together the flour, baking powder, salt, and cinnamon.

Step 5: Combine Wet & Dry

Gradually add the dry ingredients to the wet mixture, stirring until a soft dough forms.

Step 6: Fold in Pineapple

Gently fold in the crushed pineapple until evenly distributed. The dough will be soft and slightly sticky.

Step 7: Scoop & Shape

Scoop tablespoon-sized portions of dough onto the prepared baking sheet, spacing them about 2 inches apart.

Step 8: Add Cherries & Caramel

Press half a maraschino cherry into the center of each cookie, then drizzle a small amount of caramel sauce over the top.

Step 9: Bake

Bake for 12-15 minutes, or until the edges are golden brown and the cookies are set.

Step 10: Cool & Serve

Let the cookies cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.

Notes

Drain the pineapple well – Too much moisture can make the dough too soft.
Chill the dough for 10 minutes if it’s too sticky.
Use parchment paper to prevent sticking.
Let cookies cool completely before storing to avoid sogginess.