Pineapple Upside-Down Cupcakes

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📝 Description:

These moist cupcakes feature caramelized pineapple slices and maraschino cherries on top, baked upside down for a beautiful glossy finish. Each bite offers sweet pineapple, buttery cake, and a hint of caramel — a delightful tropical treat in cupcake form.

🌍 Origin:

Pineapple upside-down cake is a classic American dessert from the early 20th century, popularized in the 1920s and ’30s. This cupcake version captures all the flavor and charm but in a fun, portable portion.

🥄 Ingredients (Makes 12 cupcakes):

For the Topping:

  • Unsalted butter – ¼ cup (57g)
  • Brown sugar (packed) – ½ cup (100g)
  • Pineapple slices (canned or fresh) – 12 small rings (or cut fresh pineapple to fit cupcake tins)
  • Maraschino cherries – 12

For the Cake:

  • All-purpose flour – 1½ cups (180g)
  • Baking powder – 1½ teaspoons
  • Salt – ¼ teaspoon
  • Unsalted butter (softened) – ½ cup (113g)
  • Granulated sugar – ¾ cup (150g)
  • Eggs – 2 large
  • Vanilla extract – 1 teaspoon
  • Whole milk – ½ cup (120ml)
  • Pineapple juice (from the can or fresh) – ¼ cup (60ml)

🌿 Optional Ingredients:

  • Cinnamon – ½ teaspoon (in topping or batter)
  • Toasted coconut flakes – for garnish
  • Cream cheese frosting – for serving (optional)

👩‍🍳 Instructions:

  1. Prepare topping:
    Preheat oven to 350°F (175°C).
    In a small saucepan, melt butter and brown sugar over medium heat until bubbly and combined.
    Spoon about 1 tablespoon of this mixture into each cupcake liner.
    Place a pineapple ring on top of the sugar mixture in each liner, then top each ring with a maraschino cherry.
  2. Prepare cake batter:
    In a bowl, whisk together flour, baking powder, and salt.
    In a separate bowl, cream softened butter and sugar until light and fluffy.
    Beat in eggs one at a time, then vanilla.
    Alternate adding the flour mixture and milk, beginning and ending with flour. Mix until just combined.
    Stir in pineapple juice.
  3. Fill cupcake tins:
    Spoon batter over the pineapple topping in each cupcake liner, filling about ⅔ full.
  4. Bake:
    Bake for 18–22 minutes, or until a toothpick inserted into the center comes out clean.
  5. Cool and invert:
    Let cupcakes cool in the pan for 10 minutes.
    Run a knife around the edges, then carefully invert cupcakes onto a cooling rack or plate so the pineapple topping is on top.
  6. Serve:
    Enjoy warm or at room temperature. Optionally top with whipped cream or cream cheese frosting.

💡 Tips for Success:

  • Use a non-stick or silicone muffin pan for easy removal.
  • Don’t overfill cupcake liners to prevent overflow.
  • Let cupcakes cool slightly before inverting to avoid sticking or breakage.

📌 Recommendation:

These cupcakes pair beautifully with iced tea or a tropical cocktail. Perfect for summer parties or a fun dessert option!

🔍 Nutrition (Per Cupcake, approx.):

  • Calories: ~250
  • Fat: 10g
  • Carbs: 35g
  • Protein: 3g
  • Sugar: 20g
  • Sodium: 150mg

Want a gluten-free or vegan version? Or a pineapple upside-down cake instead?

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