Preheat the oven to 350-degrees F, and spray a 9-inch round cake pan generously with cooking spray.

In a small saucepan, combine the butter and brown sugar. Melt over low heat while stirring occasionally until smooth. Stir in the vanilla and scrape into the bottom of the cake pan.

Arrange the pineapple rings in a single layer on top of the butter-brown sugar. Place a maraschino cherry in the center of each ring.

In a small bowl, whisk together the flour, baking powder, and salt. Set aside.

In a medium bowl, add the softened butter and granulated sugar. Beat with an electric mixer until smooth and fluffy, at least 1 minute.

Add the eggs, vanilla, and pineapple juice and beat to combine.

Sprinkle the flour mixture on top, and beat just to combine.

Gently scrape the batter on top of the pineapple rings, smooth the top, and bake for 45 minutes.

Test after 45 minutes using a toothpick that you only insert in the top layer of the cake. The cake is done when the toothpick is mostly clean and the cake is starting to pull away from the sides of the pan.

Let the cake cool in the pan for about 20 minutes, place a plate on top, and invert the pan over the plate. Tap down firmly to help the cake release from the pan.

If it doesn’t release, place it back in the oven for a few minutes and try again.