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Pineapple Upside Down Cupcakes

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Pineapple Upside Down Cupcakes are a delightful twist on the classic dessert, featuring caramelized pineapple rings and maraschino cherries atop moist, buttery cake in individual portions.

Ingredients

  • Pineapple slices (canned or fresh) – 12 slices
  • Maraschino cherries – 12
  • Brown sugar – 1/2 cup
  • Butter – 1/4 cup (melted, plus extra for topping)
  • All-purpose flour – 1 1/2 cups
  • Baking powder – 1 1/2 tsp
  • Salt – 1/4 tsp
  • Granulated sugar – 3/4 cup
  • Eggs – 2 large
  • Milk – 1/2 cup
  • Vanilla extract – 1 tsp

Instructions

  1. Preheat the oven to 350°F (175°C) and grease a muffin tin or line with cupcake liners.
  2. In a small saucepan, melt butter and stir in brown sugar until combined and bubbly.
  3. Spoon a little of the brown sugar mixture into each muffin cup.
  4. Place a pineapple slice and a maraschino cherry in each muffin cup on top of the brown sugar mixture.
  5. In a mixing bowl, whisk together flour, baking powder, and salt.
  6. In another bowl, beat together granulated sugar, eggs, milk, melted butter, and vanilla extract until smooth.
  7. Gradually add the dry ingredients to the wet ingredients, mixing gently until just combined.
  8. Spoon the batter evenly over the pineapple and cherry in each muffin cup.
  9. Bake for 20-25 minutes or until a toothpick inserted into the center comes out clean.
  10. Allow cupcakes to cool for 5 minutes, then invert onto a serving plate so the pineapple topping is visible.

Notes

  • For extra warmth, add a sprinkle of cinnamon to the brown sugar mixture.
  • Swap maraschino cherries with fresh raspberries or blueberries for variation.
  • Substitute some milk with coconut milk for a richer tropical flavor.
  • Store cupcakes in an airtight container at room temperature for up to 2 days or refrigerate for up to 5 days.
  • Reheat gently in the microwave for 10-15 seconds to restore softness.
  • Use fresh pineapple by cutting into rings or pieces and softening before baking.
  • For gluten-free, substitute all-purpose flour with a gluten-free flour blend.
  • To prevent sticking, grease muffin tins well or use silicone liners and let cupcakes cool briefly before inverting.
  • Dairy-free options include using plant-based butter and milk like almond or coconut milk.
  • Freeze cupcakes up to 2 months in airtight containers; thaw overnight in the fridge before warming.

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