Pineapple Upside Down Cupcakes

A perfect vanilla cupcake made better with a fresh pineapple baked in and covered with biscuit crumb frosting.


  • 429 grams all-purpose flour
  • 265 grams caster (superfine) sugar
  • 1/2 teaspoon salt
  • 3 teaspoons baking powder
  • 375 milliliters of milk
  • 125 milliliters vegetable oil
  • 125 grams unsalted butter, softened
  • 2 tablespoons Greek yogurt (can substitute with sour cream)
  • 1 teaspoon vanilla extract
  • 2 large eggs
  • X20 Pineapple rings
  • X20 glace cherries
  • X20 maraschino cherries
  • Brown sugar to sprinkle
  • Crumb mixture
  • 10 vanilla cookies (any kind)
  • 1/4 cup brown sugar
  • Frosting
  • 1 batch fluffy vanilla buttercream frosting


  1. Crumb mixture
  2. Combine crushed cookies and brown sugar together
  3. Preheat a fan-forced oven to 160C (320F) or 180C (356F) for a conventional oven. Line a cupcake tin with cupcake liners.
  4. In the bowl of a stand mixer fitted with the paddle attachment, add the flour, baking powder, caster sugar and salt. Turn mixer on low speed and allow it to mix for a couple minutes to help everything combine well (alternatively you may do this by sifting the ingredients together). Add the softened butter and let it mix until it resembles a fine sand like texture.
  5. Next, add milk, eggs, yogurt, oil and vanilla extract in a large jug and whisk well.
  6. Add wet ingredients to dry ingredients in a slow and steady stream until no dry ingredients are visible. Scrape down the bowl and mix for another 20 seconds.
  7. Fill each cupcake liner 3/4 of the way (using an ice cream scoop to transfer the batter into the cupcake liners makes this a quick and easy process otherwise you can use two tablespoons).
  8. Place a ring of pineapple on top of each cupcake and a glace cherry in the centre. Sprinkle with about a teaspoon of brown sugar on top of each cupcake.
  9. Bake for 20-25 min or until a toothpick inserted comes out clean. Allow them to cool completely on a wire cooling rack before frosting.
  10. Sprinkle another teaspoon of brown sugar on top of each baked cupcake. Use a kitchen torch to caramelise each cupcake. Allow to cool
  11. Fit the end of a piping bag with a round top and frosting a swirl of frosting on top. Dip frosting in biscuit and brown sugar mixture. Fit the end of a piping tip with a Wilton !M tip and frost a swirl on top of the crumbed frosting. Finish off with a maraschino cherry on top.