Description

These From Scratch Pineapple Upside Down Cupcakes are a delightful twist on the classic dessert, offering individual portions with moist vanilla cupcakes topped with caramelized brown sugar, buttery pineapple, and cherries. Perfect for parties or a sweet treat, they combine the tropical tang of pineapple with a rich, buttery topping for a deliciously nostalgic bite-sized dessert.

Ingredients

Scale

Topping

20 oz pineapple slices (canned, or pieces; if using slices you need 2 cans)
½ cup unsalted butter
¾ cup brown sugar
Maraschino cherries (1 jar)

Cupcakes

1 ¼ cup all-purpose flour (160g)
¾ cup granulated sugar (150g)
1 tsp baking powder
¼ tsp baking soda
½ tsp kosher salt
¾ cup pineapple juice (reserved from canned pineapple)
¼ cup vegetable oil
1 large egg
2 tsp vanilla extract (optional)

Instructions

Preheat and Prepare Pan: Preheat your oven to 350° F (175° C) and spray a muffin tin with baking spray containing flour to prevent sticking.
Drain Pineapple: Drain the canned pineapple, setting aside ¾ cup of the juice for the batter. Pat the pineapple slices or pieces dry to remove excess moisture.
Make Caramel Mixture: In a small saucepan over low to medium heat, melt ½ cup unsalted butter and ¾ cup brown sugar together until combined and smooth.
Layer Base: Spoon about 1 tablespoon of the brown sugar and butter mixture into the bottom of each muffin tin cup.
Add Pineapple and Cherries: If using pineapple slices or rings, place one ring at the bottom of each muffin cup and place a maraschino cherry in the center. If rings are too large, cut into chunks. For pineapple chunks, arrange 3-4 pieces around the bottom with a cherry in the center.
Mix Dry Ingredients: In a large bowl, whisk together 1 ¼ cup all-purpose flour, ¾ cup granulated sugar, 1 teaspoon baking powder, ¼ teaspoon baking soda, and ½ teaspoon kosher salt.
Combine Wet Ingredients: Add the reserved ¾ cup pineapple juice, ¼ cup vegetable oil, 1 egg, and 2 teaspoons vanilla extract (optional) to the dry ingredients. Mix gently until all ingredients are just combined, taking care not to overmix.
Fill Muffin Cups: Spoon the batter into each muffin cup, filling them about ⅔ full. Avoid overfilling to prevent spilling and uneven baking.
Bake: Place the muffin tin in the oven and bake for 18 minutes, or until a toothpick inserted in the center comes out clean.
Cool in Pan: Let the cupcakes cool in the pan for about 10 minutes. Then, run a knife around the edges of the muffin cups to loosen the cupcakes.
Invert Cupcakes: Position a wire rack over a parchment-lined sheet tray. Invert the cupcakes onto the wire rack to reveal the pineapple upside down tops. Allow them to cool completely.
Garnish and Serve: Optionally top the cooled cupcakes with whipped cream or a light dusting of powdered sugar before serving for extra sweetness and presentation.

Notes

Make sure to pat the pineapple dry to reduce excess moisture and avoid soggy cupcakes.
Use a muffin pan sprayed with flour-based baking spray to ensure easy removal of cupcakes after baking.
The optional vanilla extract adds depth of flavor but can be omitted if unavailable.
These cupcakes are best enjoyed the same day for optimal texture but can be stored in an airtight container for up to 2 days.
You can substitute vegetable oil with melted coconut oil for a slight tropical twist.
For a gluten-free version, substitute the all-purpose flour with a gluten-free flour blend at a 1:1 ratio.

Prep Time: 15 minutes
Cook Time: 18 minutes
Category: Dessert
Method: Baking
Cuisine: American

Nutrition

Serving Size: 1 cupcake
Calories: 280 kcal
Sugar: 22 g
Sodium: 180 mg
Fat: 12 g
Saturated Fat: 5 g
Unsaturated Fat: 6 g
Trans Fat: 0 g
Carbohydrates: 38 g
Fiber: 1 g
Protein: 2 g
Cholesterol: 35 mg

Keywords: pineapple upside down cupcakes, pineapple cupcakes, upside down cake, individual cupcakes, tropical dessert, maraschino cherries dessert