Pineapple Upside-Down Cake

Step 1

Heat oven to 350 degrees.

Step 2

Prepare the topping: In a medium bowl, whisk together sugar, butter, vanilla extract and cinnamon (if using). Pour the mixture into an ungreased 9-inch pie dish or round cake pan that’s at least 2 inches deep.

Step 3

Using a clean kitchen towel or a paper towel, blot any excess liquid off the fruit. Arrange the pineapple slices to your liking in a single layer on top of the brown sugar-butter mixture, covering the base of the pan, then add the cherries wherever there’s a gap. Place the pan in the refrigerator while you prepare the rest of the cake.

Step 4

Prepare the cake: In a medium bowl, whisk together the cake flour, baking powder, baking soda and salt; set aside.

Step 5

Using a handheld mixer or stand mixer fitted with a paddle or whisk attachment, beat the butter on high speed until creamy, about 1 minute. Add sugar and beat on high speed until creamed together, about 1 minute, scraping down the sides and the bottom of the bowl with a rubber spatula as needed.

Step 6

On high speed, beat in the eggs, one at a time, until combined, then beat in the yogurt and vanilla extract, scraping the bowl as needed.

Step 7

Pour the dry cake flour mixture into the wet ingredients. Turn the mixer to low speed and carefully pour in the milk. Beat on low speed just until all the ingredients are combined. Do not overmix. You may need to whisk it all by hand to make sure there are no lumps at the bottom of the bowl. The batter will be slightly thick.

Step 8

Remove the pan from the refrigerator. Pour and spread the cake batter evenly over the topping.

Step 9

Bake for 40 to 55 minutes. The cake is done when a toothpick inserted into the center comes out mostly clean. (A couple moist crumbs are OK.)

Step 10

Remove cake from the oven and cool on a wire rack for 20 minutes. Run a knife along the edge to loosen, then invert the cake onto a plate. (Take care, as the pan may still be hot.) Serve warm or at room temperature.