Preheat your oven to 350°F (175°C) and grease and line the bottoms of 12 jumbo muffin tins with parchment paper rounds.

In a small saucepan over medium heat, combine 1/2 cup of butter and brown sugar. Once the butter has melted, whisk into the brown sugar until smooth and lightened in color.

Spoon a heaping tablespoon of the brown sugar mixture into the bottom of each muffin tin round.

Gently push a pineapple ring into the sugar mixture and add a cherry in the center. Repeat with the remaining muffin tin rounds. Set aside.

In a bowl, whisk together the flour, baking powder, allspice, baking soda, and salt. Set aside.

In a stand mixer fitted with the paddle attachment, cream the 3/4 cup butter until light and fluffy, then add the granulated sugar and continue mixing until well incorporated.

Add vanilla and the eggs, one at a time, ensuring each egg is fully incorporated before adding the next.

Gradually add the flour mixture to the stand mixer bowl, mixing on low speed until fully incorporated.

Using a large 3-tablespoon cookie scoop, dollop the batter onto the pineapple rings in each muffin cup, filling each two-thirds full. Use an offset spatula to even out and spread the batter to the sides.

Bake on the middle rack for 20-25 minutes or until the tops appear golden and the cupcake springs back when lightly touched.

Remove from the oven, place on a wire cooling rack, and brush the tops of each cupcake with the reserved pineapple juice, allowing it to soak in.

After cooling for 10-15 minutes, loosen the sides with a small sharp knife, then invert onto a serving platter until ready to serve.