I have a strong association of pineapple upside down cake with major sporting events, so I’m thinking of it as a great World Series dessert. When I was in high school we would always go to the same friend’s house for the Super Bowl and every year his mom would make (among many bacon wrapped items) pineapple upside down cake. Looking back I actually don’t remember ever eating a pineapple upside down cake that wasn’t made by Mrs. Fernando until I started making them myself. A couple years ago I texted my friend to ask for the recipe and he said that while she was touched I was asking (more than 10 years after high school) she uses a box mix. Now I’ve come a long way in getting over my general snobbery so I have nothing against box mixes anymore but I thought it would be fun to come up with my own recipe and add some tropical and warming flavors to make the cake more pineapple appropriate and less 1950s vanilla cake meeting canned tropical fruit for the first time (not that there’s anything wrong with that if you’re in the mood for it).



Tips
Butter
You’ll notice this recipe called for a total of 7 tablespoons of butter, leaving one lone tablespoon left over from the stick. If you’re like me and this drives you nuts (my fridge is full of butter stick ends) you can either use the tablespoon to grease the cake pan or you can throw it in with the melted butter and take the butter to barely browned to reduce the volume a touch and add some nutty flavor.
Flipping

Flipping the cake is obviously the scariest part of any upside down dessert, but I think I’ve minimized the risk with my technique. To prepare to take the cake out of the oven lay a folded kitchen towel on the counter with a cooling rack on top. Have your serving plate to the side. When you take the cake out of the oven place it on the cooling rack. This way you can slide your hand under the kitchen towel and get a good base under the cake without dealing with hot pans or oven mitts. Put the plate upside down and flip. If you want to go the extra step I put the whole contraption on a large cutting board so I wouldn’t be bring the plate down on a hard counter but on a soft wooden surface.
Spiced Pineapple Upside Down Cake Recipe
Ingredients
Topping
- 4 tablespoons butter
- 1/2 cup (106 g) light brown sugar OR 1/3 cup (75 g) jaggery*
- 1/4 teaspoon ground cinnamon (preferably from Ceylon)
- 1/4 teaspoon ground ginger
- 1/2 of a fresh pineapple, sliced thinly and cut into whatever shapes you’d like
Cake
- 3 tablespoons room temperature butter
- 3/4 cup (150 g) granulated sugar
- 1 large room temperature egg
- 1 teaspoon vanilla extract or dark rum
- 1/8 teaspoon coconut extract/flavor
- zest of 1 large lime
- 1 1/3 cups (160 g) all purpose flour
- 1/2 teaspoon salt
- 2 teaspoons baking powder
- 1/2 teaspoon ground cardamom
- 1/4 teaspoon ground nutmeg
- 1/2 cup (113 g) coconut milk
Instructions
- Preheat oven to 375 F. Grease a 9″ round cake pan. It’s important to be thorough to make flipping as easy as possible.
- Make the topping: In a small bowl mix together the brown sugar/jaggery, cinnamon and ginger. Melt the butter then pour it over the sugar mix and stir until it makes a paste. Spread across the bottom of your prepared pan, covering completely. Arrange pineapple in whatever fun design you like.
- Cake: With a hand mixer in a large bowl or in a stand mixer beat the butter and sugar until smooth. Add the egg, vanilla/rum, coconut flavoring and zest, beat to combine.
- In a medium bowl whisk together flour, salt, baking powder, cardamom and nutmeg. Shake the coconut milk can before opening and pouring into a measuring cup.
- With the mixer on low alternate the flour mixture and coconut milk in three additions to the butter/sugar/egg, scraping the bowl down between each addition. When everything is combined beat at medium speed briefly to fully combine and aerate.
- Pour the thick batter into the cake pan (the pineapples should be well stuck in the cooled sugar/butter so they don’t shift under the batter). Spread to the edges and tap the pan on the counter to release air bubbles trapped between the pineapple pieces.
- Bake for 35 minutes. If you use a cake tester, make sure you don’t hit the pineapples/caramel when you poke the cake and it will appear wet and underbaked.
- Remove from oven and wait 3 minutes. If the cake does not pull away from the sides when you touch it, run a thin knife around the edge. Flip cake. Cover with towel and tap gently all around the cake pan before carefully removing. You can wait to remove until the pan cools very slightly to make it a little easier.

*Jaggery is unrefined cane sugar common in the Indian subcontinent. It is produced by boiling cane syrup so is less processed (similar process to maple syrup) and more flavorful that refined sugars (which has the molasses removed). It has a bit of a fruity flavor which pairs well with the pineapple and breaks down into syrup easily which makes it great for caramel. It also has actual vitamins and minerals unlike refined sugar, including potassium, calcium, magnesium and iron. Basically health food.