Go Back
+ servings
A square white platter holds four jumbo pineapple upside-down muffins, each crowned with a maraschino cherry with the stem, surrounded by extra cherries.
Print Recipe
4 from 2 votes

Jumbo Upside-Down Pineapple Muffins

Jumbo upside down pineapple muffins with caramelized brown sugar, juicy pineapple rings, and cherries; sweet, tropical, and bakery-style in every bite.
Prep Time10 minutes
Cook Time20 minutes
Total Time30 minutes
Course: Dessert
Cuisine: American
Keyword: pineapple muffins, upside down pineapple muffins
Servings: 12 large muffins
Author: Lisa Kerhin

Ingredients

For the Muffins:

  • 1 ½ cups flour
  • 2 ¼ tsp baking powder
  • ½ tsp cinnamon
  • ¼ tsp salt
  • 2 tbsp cornstarch
  • 4 eggs
  • cups sugar
  • ¼ cup brown sugar, packed
  • ½ cup pineapple juice, use the juice from the pineapple can
  • 2 tsp vanilla

For the Topping:

  • 6 tbsp unsalted butter
  • 1 ½ cups dark brown sugar, packed
  • 1 tsp vanilla
  • 12 pineapple rings, you'll need one 20 oz can and one 8 oz can
  • 12 maraschino cherries, with stems

Instructions

  • Prep the Pan and Dry Mix: Preheat your oven to 350 degrees. Spray a jumbo muffin pan generously with non-stick spray.
    In a medium bowl, whisk together the flour, baking powder, cinnamon, salt, and cornstarch; set this dry mix aside.
  • Make the Topping: In a small saucepan, melt the butter over medium heat. Stir in the brown sugar and vanilla, and whisk for one minute until the mixture is smooth and slightly bubbling. Remove immediately from the heat.
  • Assemble the Topping Base: Spoon about 2 tablespoons of the warm topping mixture into the bottom of each prepared jumbo muffin cup.
    Center a pineapple ring over the topping in each cup, then place a single maraschino cherry in the middle of each pineapple ring.
  • Create the Batter: In a large bowl, combine the eggs, both sugars (granulated and brown), and vanilla extract, and beat until the mixture is smooth.
    Stir in the pineapple juice until fully combined. Gradually add the reserved dry ingredients, mixing only until just combined. Stop mixing as soon as the flour disappears to prevent a dense muffin.
  • Bake and Invert: Divide the batter equally among the prepared muffin cups, filling each one about 3/4 full. Bake for 20-23 minutes, or until the muffins are golden brown and a toothpick inserted into the center comes out clean.
    Let them cool in the pan for about 5 minutes, then run a knife around the edge of each muffin to ensure easy release. Place a cooling rack over the pan and quickly flip it over to release the muffins onto the rack.
    Gently lift the cherry stem on each muffin so it stands up. Serve warm or at room temperature.

Notes

Pro-Tip for Easy Cleanup: Place a sheet of parchment or wax paper under your cooling rack before inverting the pan to catch any sticky caramel topping.