Pineapple upside-down cupcakes feature a fluffy vanilla cupcake base topped with caramelized pineapple and cherries. They taste just like the cake, but are faster and more portable!

Recipe: https://sugarspunrun.com/pineapple-up...

Ingredients
For the topping
6 Tablespoons salted butter, melted (85g)
12 Tablespoons light brown sugar, firmly packed (150g)
2 ⅓ cups pineapple chunks, drained/patted dry (438g) (see note)
12 Maraschino cherries, drained
For the cupcakes
½ cup unsalted butter, softened to room temperature (113g)
¾ cup granulated sugar (150g)
2 large eggs, room temperature preferred
1 teaspoon vanilla extract
1 ½ cups all-purpose flour (187g)
1 ½ teaspoons baking powder
¼ teaspoon table salt
½ cup buttermilk (118ml)

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Instructions
00:00 Introduction
00:10 Preheat oven to 350F (175C). Evenly divide butter into the bottom of each cupcake well and use a pastry brush to lightly brush the sides with butter as well.
01:23 Sprinkle 1 Tablespoon (12 grams) of sugar evenly into the bottom of each cupcake well.
02:15 Arrange 4 pineapple chunks in a flower pattern over the butter and brown sugar and press a Maraschino cherry into the center of each “flower.” Set aside as you prepare your cupcake batter.
For the cupcakes
03:40 Combine butter and sugar in a medium-sized mixing bowl (or the bowl of a stand mixer fitted with the paddle attachment) and use an electric mixer to beat until light and fluffy.
04:15 Add eggs and vanilla extract and beat well.
05:00 In a separate mixing bowl, whisk together flour, baking powder and salt.
05:33 Alternate adding the flour mixture and the buttermilk to the batter, starting and ending with the flour mixture and stirring until just combined after each addition (I add the flour mixture in 4 parts and the buttermilk in 3 parts and recommend doing this part gently by hand with a spatula to not over-mix).
06:28 Evenly divide the cupcake batter into your prepared pan, filling each cupcake well to the rim (don’t overfill, if you have excess batter discard it). The batter will be thick, so use a spoon to gently spread it into each cupcake well.
07:25 Place cupcake tin on a foil lined rimmed baking sheet (in case of spills) and transfer to center rack of 350F (175C) preheated oven and bake for 22-25 minutes and a toothpick inserted in the center comes out clean or with moist crumbs.
07:42 Allow cupcakes to cool in pan for 5 minutes then use a knife to gently loosen the cupcake from the edges of the pan before inverting. Place a wire cooling rack over the cupcake tin and, carefully, using potholders (the tin will be very hot!) keep the cooling rack pressed securely against the tin and invert cupcakes onto cooling rack. Lift the tin, the cupcakes should release easily.
08:57 Allow to cool a bit before serving. These are great served warm and we love them with vanilla ice cream, too!

Notes
Pineapple chunks
I use canned pineapple chunks in 100% pineapple juice. Drain the pineapple chunks and pat dry. I find a single can is usually not enough, you’ll need at least 21 oz of canned pineapple chunks.
Doubling
You can easily double this recipe for 24 cupcakes.
Storing
Store in an airtight container in the refrigerator and enjoy within 2-3 days.

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