Preheat your oven to 350 F (175 C). Take a 9" round cake pan that's at least 2" high and add 4 tbsp of melted unsalted butter on the bottom surface. Use a brush to spread it evenly over the bottom surface and up the sides of the pan.

Sprinkle 1/2 packed cup of dark brown sugar over the bottom surface.

Line a sheet pan with paper towels. From a 20-oz can of pineapple slices in pineapple juice (not syrup), separate the pineapple slices and the juice. You should get about 10 round slices and around 1 cup of pineapple juice. Set the pineapple juice aside for now. Extract 19 maraschino cherries from a jar. Place the pineapple slices and maraschino cherries on the paper towel-lined sheet pan and pat the pineapple slices and maraschino cherries with extra paper towels to remove excess juices. The fruit should be as dry as possible before baking to avoid a soggy cake.

Arrange 7 round slices on the bottom of the prepared pan on top of the brown sugar. I like to put 1 round in the middle, and the remaining 6 around the perimeter of the pan, in a tessellated pattern. Take the 3 remaining rounds and slice them in half to make 6 halves. Arrange these halves along the side of the pan.

Arrange the blotted maraschino cherries in the middle of the pineapple rounds as well as in the gaps where three rounds of pineapple meet. You'll need exactly 19 maraschino cherries. Be sure to press the pineapples and cherries firmly into the pan so they are in direct contact with the bottom surface of the pan. This will ensure that the top of the cake has more vibrant colors from the pineapple and cherries. Place this prepared pan in the fridge to help the topping arrangement set while making the cake batter.

Take a large bowl and sieve, add in 1 1/2 cups of all-purpose flour, 1 tsp of baking powder, 1/4 tsp baking soda, and 1/2 tsp of salt. Sift together and whisk the dry ingredients together to combine.

In a medium bowl, add in 1/3 cup of sour cream, 2 tsp of vanilla extract, 1/4 cup of pineapple juice from the can that was set aside earlier, and 2 tbsp of milk (we use almond milk). Whisk these wet ingredients together till well combined.

In the bowl of your stand mixer, add in 8 tbsp (1 stick) of softened unsalted butter and 3/4 cup of granulated sugar. With the paddle attachment, beat on medium-high speed for 2 minutes till the butter and sugar are creamed together. Stop the mixer. Scrape down the sides and bottom of the mixing bowl as needed.

While mixing on medium speed, add in 2 large eggs, one egg at a time, making sure the first egg is fully incorporated before adding the second one. Stop the mixer and scrape down the bowl as needed. Then mix on medium speed for another 20 seconds to let the wet ingredients incorporate completely.

Turn the speed down to low, add in about one-third of the flour mixture, mixing it until just combined. Then add half of the sour cream mixture, mixing until just combined. Continue alternating with remaining flour and sour cream mixture. Mix on low just until everything is well combined and the batter looks smooth. Try not to overmix this batter. Stop the mixer and scrape down the paddle attachment and bowl as needed.

Pour this batter into the prepared pan that's been chilled. Level the top surface with an offset spatula, spreading the batter all the way to the sides to completely cover the half-rounds of pineapple on the sides of the pan. Before placing the cake in the oven, take a piece of foil and mold it over the top of the pan. Remove the foil.

In the preheated oven at 350 F (175 C), bake this uncovered for a total 30 minutes. At the 30-minute mark, add the molded foil loosely over the pan. This will prevent the top surface (which will be the bottom of the cake) from getting burned as the center of the cake finishes cooking. The cake will rise and stick to the foil a bit, and that's okay. Continue baking with the foil top for another 12 to 15 minutes.

Remove the foil. The cake is done when a toothpick inserted in the center comes out with just a few moist crumbs. and let the cake cool in the pan on a metal rack for 20 minutes. After it has cooled for 20 minutes, take your serving dish or plate and put it over the cake. Quickly and confidently invert the cake directly onto the serving dish. Tap the base of the cake pan, gently shake the pan as needed, and slowly and very gently lift off the cake pan.

Let the cake cool completely to room temperature before slicing. Serve at room temperature. Cover leftovers in an airtight container and will keep in the fridge for up to 5 days. Enjoy!