Rating: 2.5 stars
2 Ratings
  • 5 star values: 0
  • 4 star values: 1
  • 3 star values: 0
  • 2 star values: 0
  • 1 star values: 1

Enjoy this Southern classic in adorable cupcake-sized portions.


Credit: Micah A. Leal

Recipe Summary test

30 mins
55 mins
12 Cupcakes

When we're talking desserts, sometimes it's just better to go the single-serving route. No sharing and no wondering if you're being greedy with a too-big slice? That's just our speed. We remade one of our favorite Southern dessert recipes into cupcake-sized portions to shouts of glee. They're cute, they're sweet, and they're ready to be devoured in the blink of an eye. As with any upside-down dessert, inverting the cake once it's baked is usually the hairiest part of the process. Avoid the nail-biting by lining each of the wells in the cupcake pan with parchment paper prior to adding the fruit and batter. Two more tips before we leave you to this bookmark-able recipe: first, serve them warm and, second, go ahead and make a second batch—like immediately.


Ingredient Checklist


Instructions Checklist
  • Preheat oven to 350°F. Grease a standard-size nonstick 12-cup muffin pan with cooking spray.

  • In the bowl of a stand mixer, stir together flour, sugar, baking powder, and salt. Add butter and beat on low speed with paddle attachment until fully incorporated into flour, about 3 minutes.

  • In a separate bowl, whisk together buttermilk, egg yolks, egg, 2 Tbsp. reserved pineapple juice, oil, and vanilla. Add half of the liquid ingredients to the mixer and beat on medium-low for 2 minutes. Scrape down the sides of the bowl, add remaining liquid ingredients and beat on medium for 3 minutes.

  • Place 1 teaspoon of brown sugar in each of the muffin cups, using your finger to evenly spread the sugar across the bottoms of each cup. On top of the brown sugar, place three pineapple chunks around the edge of the bottom of each muffin cup. Place a maraschino cherry in the center of each muffin cup. Evenly divide cake batter among muffin cups, dumping batter directly on top of brown sugar, pineapple, and maraschino cherries.

  • Bake until golden brown and a toothpick inserted comes out clean, 23 to 25 minutes. Remove from oven and immediately run an offset spatula or knife around the edge of each cupcake. Place a baking sheet on top of the muffin pan and quickly flip the baking sheet and muffin pan so that the Pineapple Upside-Down Cupcakes cleanly come out of the pan. Serve warm.