Pineapple Upside‑Down Sugar Cookies 

These Pineapple Upside‑Down Sugar Cookies are a playful spin on the classic cake, turning the iconic flavors of pineapple, brown sugar, and cherry into a handheld cookie. Soft sugar cookie dough is baked in individual mini pans or muffin cups, topped underneath with brown sugar, pineapple slices, and maraschino cherries. As they bake, the sugar caramelizes around the fruit, infusing each cookie with tropical sweetness. Once inverted, they reveal a glossy, gooey pineapple-cherry crown on a fluffy cookie base. Perfect for summer gatherings, brunch, or whenever you crave a tropical treat. 

Ingredients

• 1 cup unsalted butter, softened
  
  

• 1 cup granulated sugar
  
  

• 2 large eggs
  
  

• 2 tsp vanilla extract
  
  

• ½ cup sour cream
  
  

• 3 cups all‑purpose flour
  
  

• 1 tsp baking powder
  
  

• 1 tsp cornstarch
  
  

• ½ tsp salt
  
  

• 13 canned pineapple slices, drained
  
  

• 13 maraschino cherries
  
  

• ½ cup packed light brown sugar
  
  

• ½ cup melted butter (for topping)
  
  

Directions

1. Preheat oven to 350 °F (≈ 175 °C). Grease or line mini round pans or muffin cups.
   
   

2. In a baking dish or separate bowl, whisk together melted butter and brown sugar. Spoon about 1 Tbsp into each cup to form the topping layer.
   
   

3. Top each with one pineapple slice and one cherry centered inside.
   
   

4. In a mixing bowl, cream together softened butter and granulated sugar until light and fluffy. Add eggs, vanilla, and sour cream; mix until combined.
   
   

5. Add flour, baking powder, cornstarch, and salt; mix until just combined to form cookie dough.
   
   

6. Place a generous scoop (~3 Tbsp) of cookie dough over each fruit‑topped cup, spreading it gently to cover. 

7. Bake for about 25 minutes, until the edges of the cookies are golden and the brown sugar is bubbling.
   
   

8. Let cool in pan about 10 minutes, then invert onto wax paper to allow caramel to set. If fruit sticks, reposition gently. Cool completely before serving.
   
   

Nutrients

(Estimated per cookie; recipe yields ~13 cookies)

• Calories: ~519 kcal
  
  

• Carbohydrates: ~73 g (Sugars ~49 g; Fiber ~1 g)
  
  

• Fat: ~23 g (Saturated ~14 g)
  
  

• Protein: ~4 g
  
  

• Cholesterol: ~86 mg
  
  

• Sodium: ~283 mg
  
  

• Potassium: ~188 mg
  
  

• Vitamin A: ~775 IU
  
  

• Vitamin C: ~5.4 mg
  
  

• Calcium: ~66 mg
  
  

• Iron: ~1.8 mg