Preheat your grill to 500F.
Clean grill grates with a grill brush.
Cut the rind off your pineapple, and cut 8 rounds from the pineapple
*The core will be included at this stage of the process, which helps the pineapple rounds stay together when grilled.
Grill the pineapple on each side, until you get nice grill marks on both sides.
When the pineapple is grilled, transfer to a cutting board and use a paring knife or
a small metal ring mold to cut the core out from each pineapple round.
Preheat the oven to 350F (180C).
Grease the bottom and sides of a casserole dish lightly with vegetable oil.
Melt the salted butter, and mix the melted salted butter in a bowl with the brown sugar.
Pour the butter and sugar mixture into the bottom of the lightly-greased casserole dish.
Place the grilled pineapple rounds over the surface of the melted butter and brown sugar layer.
Place the maraschino cherries inside the center of each pineapple round.
In a medium-sized mixing bowl, combine the cake flour, baking powder, baking
soda, and Kosher salt, and whisk to evenly distribute the dry ingredients.
In a large mixing bowl, mix together the softened butter and white granulated
sugar until they are a uniform consistency.
*You can use a stand mixer here if that is easier for you. In baking lingo, this is
called “creaming your butter and sugar together”.
Whisk in the 2 whole eggs until they are evenly mixed.
Whisk in the sour cream, vanilla extract, and whole milk until the wet mixture is homogenous.
Add the dry ingredients into the wet ingredients, and mix well. This is your cake batter.
Pour the cake batter over the grilled pineapple base you placed in the casserole dish earlier.
Bake at 350F (180C) for about 45-50 minutes, topping with aluminum foil halfway
through if the cake starts to take on too much color.
The cake is done when a toothpick inserted into the center of the cake comes out clean.
Remove the cake from the oven, and allow it to cool at room temperature for roughly 30 minutes.
Carefully use a paring knife to make sure the sides of the cake aren’t stuck to the sides of the casserole dish.
When the cake has mostly cooled, invert the cake carefully onto a serving tray, so
that the grilled pineapple slices and maraschino cherries are now on top.
Cut the cake into slices, and serve.