The Best Pineapple Upside Down Cake

Step 1

Preheat oven to 350F.

Step 2

In a small, microwave-safe bowl, melt the butter, about 1 minute on high power.

Step 3

Pour the butter into a 9-inch springform cake pan. Use your finger to run a bit of butter around the side of the pan so it’s well-greased.

Step 4

Evenly sprinkle the brown sugar over the butter.

Step 5

Add 1 whole pineapple slice to the center of the pan.

Step 6

Halve the remaining slices vertically. Stagger them in a fan-like fashion going around the cake. I used 12 slices.

Step 7

Place the remaining slices around the sides of the cake pan with the curved side pointing down toward the bottom of the pan (see photos for reference). There will likely be bare side patches with no pineapple coverage, that’s okay.

Step 8

Place 1 cherry in the center of the whole pineapple slice in the middle of the pan.

Step 9

Place 1 cherry in the center cutout of all the fanned pineapple slices; set pan aside.

Step 10

In a large bowl, whisk together flour, granulated sugar, baking powder, optional salt; set aside.

Step 11

In a separate small bowl, whisk together the next 5 wet ingredients (through vanilla).

Step 12

Add the wet mixture to the dry, mixing lightly with a spoon or folding with a spatula until just combined. Small lumps will be present, don’t overmix or try to stir them smooth.

Step 13

Gently turn batter out into prepared pan, being careful to not disturb the pineapple slices on the sides or bottom. Fill pan only to about 3/4-full. If you have a little extra batter, discard it rather than overfilling your pan.

Step 14

Place pan on a cookie sheet (to catch anything that does overflow) and bake for about 40 minutes, or until center is set and not jiggly, and a toothpick inserted in the center comes out clean or with a few moist crumbs, but no batter. Only go down about 1-inch with the toothpick, not all the way to the bottom where you’ll hit gooey pineapple juice.

Step 15

Place pan on a wire rack and allow cake to cool for at least 30 minutes before inverting, slicing, and serving. I allowed cake to cool overnight, covered with a sheet of foil, before inverting.