Description
Soft, buttery sugar cookies topped with caramelized pineapple and maraschino cherries these Pineapple Upside-Down Sugar Cookies are a fun, bite-sized version of the classic dessert!
Ingredients
1/2 cup unsalted butter, softened
1 cup brown sugar, packed
12 pineapple rings (cut to fit muffin tin)
12 maraschino cherries
1 1/2 cups all-purpose flour
1/2 tsp baking powder
1/4 tsp baking soda
1/4 tsp salt
1/2 cup granulated sugar
1/4 cup unsalted butter, softened
1 egg
1 tsp vanilla extract
2 tbsp pineapple juice
Instructions
1. Preheat oven to 350°F (175°C) and lightly grease a muffin tin.
2. In a small saucepan, melt 1/2 cup butter and brown sugar together until combined and bubbly.
3. Spoon 1–2 teaspoons of the brown sugar mixture into each muffin cup.
4. Place a small piece of pineapple and a cherry in the center of each cup.
5. In a bowl, whisk together flour, baking powder, baking soda, and salt.
6. In another bowl, cream butter and sugar until light and fluffy.
7. Add egg, vanilla, and pineapple juice; beat until smooth.
8. Gradually mix in dry ingredients until dough forms.
9. Scoop dough into each muffin cup, covering the pineapple.
10. Bake 18–20 minutes or until golden.
11. Cool 5 minutes, then invert onto a baking sheet to release cookies.
12. Serve warm or cooled, and enjoy!
Notes
Use crushed pineapple for a rustic texture.
Add a pinch of cinnamon to the caramel mixture for extra warmth.
Store leftovers in an airtight container for up to 3 days — they stay moist and flavorful!
- Prep Time: 15 mins
- Cook Time: 20 mins
- Category: Dessert
- Method: Baked
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 210
- Sugar: 22g
- Sodium: 85mg
- Fat: 10g
- Saturated Fat: 6g
- Unsaturated Fat: 3g
- Trans Fat: 0g
- Carbohydrates: 28g
- Fiber: 0g
- Protein: 2g
- Cholesterol: 35mg
Keywords: pineapple upside-down cookies, tropical cookies, pineapple dessert, mini upside-down cakes