Preheat the oven to 350°F (175°C). While the oven is preheating, place the 1/4 cup butter in a 9×13-inch baking pan and put the pan in the oven until the butter is melted (about 3–5 minutes).

Using oven mitts, remove the hot pan from the oven and tip or spread the melted butter so it coats the bottom of the pan evenly. Set the pan on a heatproof surface.

Sprinkle the 1 cup brown sugar evenly over the melted butter.

Drain the 20 oz sliced Dole pineapple and reserve the juice. Arrange the pineapple slices in a single layer over the brown sugar in the pan.

Place one maraschino cherry (stems removed) in the center of each pineapple ring (use all 12 cherries).

Measure 1 cup of the reserved pineapple juice and set it aside for the batter.

In a mixing bowl, combine the 15.25 oz white cake mix, 3 eggs, the 1 cup reserved pineapple juice, 1/2 cup vegetable oil, and 1 teaspoon vanilla extract. Beat or whisk until the batter is smooth and no dry streaks remain.

Pour the batter evenly over the pineapple and cherries in the pan, spreading gently to cover the fruit.

Bake in the preheated 350°F oven for 30–40 minutes, until the cake is golden brown and a toothpick inserted into the center comes out clean.

Remove the pan from the oven and let it sit on a wire rack for about 5 minutes. Run a knife around the edges to loosen the cake.

Place a serving platter or cutting board over the pan. Wearing oven mitts, carefully invert the pan and platter together, then lift the pan off to release the cake. If any fruit sticks to the pan, gently loosen and reposition it on the cake.

Let the cake cool completely on the platter before slicing and serving.