Preheat your oven to 350F.
Add 1 tablespoon of light brown sugar into each cup cake mold, followed by 1 teaspoon of melted butter. After, add your maraschino cherries into each cup. Then, add your cut pineapple chunks around the cherries.
In a bowl, sift your flour, baking powder, and salt. Set aside.
In a stand mixer or bowl, add your softened butter with your sugar and mix until fluffy.
Then, add your eggs one at a time and mix.
Finally, add your vanilla, milk, and dark rum and mix until it is well incorporated.
Slowly add your dry ingredients into the wet ingredients by adding about ¼ cup at a time and making sure it is well incorporated prior to adding more.
Once your batter is done, scoop the batter into the cups on the tray which contain your cherries and pineapples. You may fill the cup almost to the top since these cupcakes are going to rise downward into the pineapples instead of up.
Bake in a preheated oven at 350F for 25 minutes or until you stick a toothpick in the center and it comes out clean.
Once done, run a knife around the edges of the cupcakes, and flip the tray, gently tapping the bottom (or now the top) of the tray to loosen the cupcakes. Serve and enjoy!