Pineapple Upside-Down Sugar Cookies – A Tropical Twist on a Classic Favorite

Pineapple Upside-Down Sugar Cookies bring all the tropical charm of the classic cake—just in adorable, handheld form. Sweet caramelized pineapple paired with soft, buttery sugar cookie dough creates a treat that’s as beautiful as it is delicious. Perfect for parties, potlucks, or whenever you want to add a fun tropical touch to dessert time, these cookies are easy to make and guaranteed to impress.

Why You’ll Love This Recipe

Tropical Flavor: Sweet pineapple + buttery cookie dough = pure joy.
Cute & Shareable: A classic cake reinvented as handheld cookies.
Crowd-Pleaser: Beautiful presentation that tastes even better than it looks.
Simple Ingredients: Pantry-friendly and quick to prepare.

Ingredients

• 1 roll (16–17 oz) refrigerated sugar cookie dough (or homemade)
• 1 can (20 oz) pineapple tidbits or small chunks, drained well
• ½ cup light brown sugar, packed
• 3 tbsp unsalted butter, melted
• 12 maraschino cherries, halved (optional, for garnish)

Instructions

1. Preheat Oven
Preheat oven to 350°F (175°C). Lightly grease a standard muffin tin or line with baking spray.

2. Prepare the Pineapple Base
In a small bowl, mix melted butter and brown sugar. Spoon about 1 teaspoon of the mixture into each muffin cup. Add a few pineapple tidbits (and half a cherry, if using).

3. Add Cookie Dough
Scoop about 1 tablespoon of sugar cookie dough and press gently on top of the pineapple mixture in each cup.

4. Bake
Bake for 12–14 minutes, or until the cookie tops are golden and set.

5. Flip & Cool
Let the cookies cool for 5 minutes, then carefully invert the muffin tin onto a baking sheet to release the cookies upside-down style.

6. Serve
Serve warm or at room temperature, and enjoy the sweet tropical flavors.

Nutritional Information

Calories: 130
Carbohydrates: 20g
Fat: 5g
Protein: 1g
Fiber: 0g

Tips for Success

• Drain Pineapple Well: Too much juice will make the cookies soggy.
• Use Muffin Tins: Keeps the shape perfect and mimics the upside-down cake effect.
• Add the Cherry: For that nostalgic, classic pineapple upside-down look.
• Serve Fresh: Best enjoyed the same day for peak flavor and texture.

Why This Recipe Works

These cookies combine the nostalgic charm of pineapple upside-down cake with the buttery simplicity of sugar cookies. The caramelized brown sugar and pineapple base creates a juicy, flavorful topping that pairs perfectly with the soft cookie underneath. It’s a dessert that’s both familiar and delightfully new.

Pineapple Upside-Down Sugar Cookies are a fun, fruity twist on a classic favorite. With their vibrant look, tropical taste, and easy prep, they’re bound to become a go-to recipe for celebrations, potlucks, or just a sweet afternoon treat. Each bite delivers sunshine in cookie form!