Ingredients
Method
- Start by preheating your oven to 350°F. Take your melted butter and pour it directly into the bottom of a 9-inch round cake pan or a cast-iron skillet. Sprinkle the brown sugar evenly over the butter. Use your fingers or a spoon to press it down into a flat layer. This is the base of your caramel.
- Lay the pineapple slices on top of the brown sugar. You can usually fit one in the center and six around the edges. If you have extra space, you can cut slices in half to fill the gaps. Place a maraschino cherry in the center of each pineapple ring.
- In a large bowl, beat the softened butter and granulated sugar together until the mixture looks pale and fluffy. Add the eggs one at a time, beating well after each addition. Stir in the vanilla extract.
- In a separate bowl, whisk your flour, baking powder, and salt together.
- Add half of the dry ingredients to the butter mixture and stir gently. Pour in the milk, then add the rest of the flour. Stir only until the white streaks of flour disappear. Over-mixing at this stage will make the cake tough and bready.
- Spoon the batter carefully over the pineapple slices. Use a spatula to spread it to the edges, being careful not to move the fruit underneath. Bake for 40 to 45 minutes.
- Let the cake rest in the pan for exactly ten minutes. Place a large plate over the top of the pan and, using oven mitts, quickly flip the whole thing over. Give the bottom of the pan a few firm taps before lifting it off.
Notes
The biggest mistake people make is using a pan that is too shallow. As the butter and sugar melt, they bubble up.
If your pan is too full, that sticky syrup will spill over onto the bottom of your oven and create a lot of smoke. Always leave at least an inch of space at the top of the pan, or place a baking sheet on the rack below to catch any drips.