2cups + 2 tbsp(263g)Cake Flour , (or all purpose flour)
2tspBaking Powder
1/4tspNutmeg
1/2tspKosher Salt
6tbspSalted Butter, (room temperature)
3tbspVegetable Oil
1cup(200g)Sugar
1/4cup(55g)Light Brown Sugar
2large(100g)Eggs, (room temperature)
1tspVanilla Extract
1tspRum Extract
1tspPineapple Emulsion, (optional)
8oz Crushed Pineapple, (drained, squeeze out as much moisture as possible)
3/4cup(180g)Buttermilk, (room temperature)
2tbspPineapple Juice, (from the canned pineapples)
1tbspMaraschino Cherry Juice, (from the jar of maraschino cherries)
Pineapple Cherry Topping
5tbspSalted Butter, (melted)
1/2cup(110g)Light Brown Sugar
20ozSliced Canned Pineapple Rings
25Maraschino Cherries
Instructions
Preheat the oven to 325 degrees F. Brush a 9x3 inch cake pan with butter, brushing the entire pan to ensure all of it is coated. Line the bottom and sides of the pan with parchment paper.
Place sliced pineapples onto a few paper towels and use an additional paper towel on top to gently press into the pineapples to remove as much moisture as possible. Do the same with the maraschino cherries on another paper towel. 20 oz Sliced Canned Pineapple Rings25 Maraschino Cherries
Now make the cake batter. Combine cake flour, baking powder, nutmeg, and kosher salt in a large bowl and whisk together. Set aside. 2 cups + 2 tbsp Cake Flour 2 tsp Baking Powder1/4 tsp Nutmeg1/2 tsp Kosher Salt
In a separate bowl, combine butter, oil, sugar, and brown sugar. Use an electric hand mixer to beat together for 2 minutes, until fully combined and pale in color. Add in the eggs, vanilla extract, rum extract, and pineapple emulsion. Continue to mix for about 1 minute, until combined, then add in the drained crushed pineapples. 6 tbsp Salted Butter3 tbsp Vegetable Oil1 cup Sugar1/4 cup Light Brown Sugar2 large Eggs1 tsp Vanilla Extract1 tsp Rum Extract1 tsp Pineapple Emulsion8 oz Crushed Pineapple
Add half of the dry ingredients and mix. Pour in the buttermilk, pineapple juice, and maraschino cherry juice, and mix until combined, about 30 seconds. Then, add the remainder of the dry ingredients. 3/4 cup Buttermilk2 tbsp Pineapple Juice1 tbsp Maraschino Cherry Juice
Pour melted butter onto the bottom of the cake pan and sprinkle brown sugar on top. Place the pineapples on top of the sugar/butter mixture, then add the maraschino cherries in the center of the pineapples and the spaces around them. For the last three pineapple slices, cut them in half and place them against the sides of the pan. 5 tbsp Salted Butter1/2 cup Light Brown Sugar
Pour the cake batter into the pan, gently so as to not disturb the pineapples, and smooth into an even layer.
Bake for 50-60 minutes, until a toothpick comes out with just a few moist crumbs. Allow the cake to cool in the pan for 8-10 minutes. Pro tip: if the cake has developed a dome in the center, just before turning over, cut the dome so that the cake is one even layer. Then turn over onto the wire rack to cool. The dome can cause the cake to crack and not set properly.
Notes
Don’t skip greasing the pan and adding the parchment lining. Upside-down cakes love to stick to pans because of the caramel topping. Butter the pan generously and line the bottom and sides with parchment to guarantee a clean flip with no sticky heartbreak.
Dry those pineapples like they owe you money! Moisture is the #1 reason upside-down cakes get gummy or fail to caramelize. Press the sliced pineapple and crushed pineapple really well. Excess liquid will dilute the brown sugar topping and make the crumb heavy.
Let it rest before flipping. This is critical! Turn the cake upside down after 8–10 minutes is the sweet spot. Too soon? The caramel leaks everywhere. Too late? The topping sticks. Tap the sides of the pan to help release suction before you invert.
Trim the dome (if it happens!). If it domes, shave that top off so the cake flips level and doesn’t crack. Professional pastry kitchens do this with every upside-down cake, it’s not “extra,” it’s insurance.