Preheat your oven to 350 degrees. Make sure to spray 12 muffin cups generously with non-stick cooking spray to ensure those cupcakes release easily.
Drain both cans of the pineapple chunks, reserving half a cup of the juice for the batter. Place the pineapple on several layers of paper towels to absorb excess moisture. This step is important to prevent soggy cupcakes.
In a microwave-safe bowl, melt one-third cup of unsalted butter. Once melted, stir in the light brown sugar until it’s well combined and syrupy. This mixture will form the delicious base for your cupcakes.
Divide this brown sugar mixture evenly among the muffin wells, adding about two teaspoons to each. Follow this by arranging pineapple chunks on top of the sugar mixture; aim for about five pieces in each well.
In a mixing bowl, whisk together all-purpose flour, granulated sugar, baking powder, and salt until well combined.
Now, attach your mixer with a paddle attachment and add unsalted butter and the reserved pineapple juice into the flour mixture. Mix until the batter is smooth and well combined, which should take about one to two minutes.
Add in the large egg and vanilla extract, mixing until these are fully incorporated into the batter.
Carefully divide the batter evenly among the muffin cups, layering it on top of the pineapple chunks, making sure to cover them completely.
Bake in your preheated oven for approximately 23 to 26 minutes, or until a toothpick inserted into the center comes out clean. As the cupcakes bake, your kitchen will fill with the most inviting aroma!
Once baked, remove the cupcakes from the oven and let them cool for five minutes. Then, run a sharp knife around the edges to loosen them from the pan.
Place a wire cooling rack over the top of the muffin pan and carefully flip it to invert the cupcakes onto the wire rack. Let them cool completely.
While the cupcakes are cooling, prepare the sweetened whipped cream. In another bowl, whip heavy cream using an electric mixer on high speed until soft peaks form. Add in granulated sugar and continue to whip until stiff peaks form.
Just before serving, pipe the whipped cream over the cooled cupcakes and top each with a maraschino cherry for that perfect finishing touch!