Place the Butter (1/4 cup) into a 9x13-inch pan and place in the oven. Preheat the oven to 350 degrees F (175 degrees C). Let the butter melt.
Once melted, remove pan from oven, and evenly sprinkle the Brown Sugar (1/3 cup) onto the melted butter. Arrange the Pineapple (12 slice) on top of the melted butter and put a Maraschino Cherry (12) in the middle of each pineapple slice. Set aside.
In a standing mixer with a paddle attachment, beat the Granulated Sugar (1 3/4 cup), Butter (1 cup), and Vanilla Extract (2 teaspoon) together on medium/high for a few minutes until the mixture is light and fluffy and white in color. While mixing on low, add the Egg (3) one at a time just until combined.
In a separate bowl, sift the All-Purpose Flour (2 1/2 cup), Salt (1 teaspoon), and Baking Soda (1 tablespoon) together. Add the dry ingredients and Buttermilk (1 1/4 cup) to the butter mixture in three additions, starting and ending with the dry ingredients.
Pour the batter on top of the pineapple-lined baking dish and spread evenly. Place the cake in the oven for 40-45 minutes or until a toothpick inserted in the center comes out clean.
Let cool for 10 minutes before turning out onto a dish or a sheet of parchment paper. Drizzle with caramel sauce if desired.