Preheat your oven to 350°F (or follow box instructions). In a large mixing bowl, combine the yellow cake mix, room temperature eggs, oil, and pineapple juice—this substitution of pineapple juice for water adds moisture and tropical flavor to the cake. Mix until just combined and smooth, being careful not to overmix. Pour the batter into a greased 9x13 inch baking dish and bake for 25-30 minutes, or until a toothpick inserted in the center comes out clean. I prefer using room temperature eggs because they incorporate more smoothly into the batter, creating a more tender crumb.

Remove the cake from the oven and let it cool in the pan for 10 minutes—this allows it to set slightly while still being warm enough to accept the liquid gelatin without crumbling. Using a fork or wooden skewer, vigorously poke holes all over the entire surface of the cake, spacing them about 1 inch apart. Don't be shy; you want plenty of holes for the gelatin to soak in and create those signature pockets of flavor and texture.

In a medium bowl, pour the 1.5 cups of boiling water over the pineapple gelatin powder and stir continuously for about 2 minutes until the gelatin is completely dissolved with no granules remaining. Let the mixture cool for 3-5 minutes so it's warm but not scalding hot. Slowly pour the gelatin liquid over the entire surface of the cake, making sure it flows into all the poked holes. Work carefully and pour in stages if needed to allow the liquid to fully absorb rather than pooling on top.

Place the cake in the refrigerator and chill for at least 45 minutes until the gelatin is completely set and no longer jiggles when the pan is gently moved. This is a critical step for proper texture—rushing it will result in a soggy topping layer.

In a large bowl, fold together the whipped topping, vanilla extract, and drained pineapple chunks until evenly combined. I like to add the vanilla extract because it enhances the tropical flavors and adds subtle depth to the topping. Gently fold rather than stir to keep the whipped topping light and airy.

Spread the pineapple-whipped topping mixture evenly over the chilled cake, working from the center outward for a neat finish. Sprinkle the toasted coconut generously over the top, then arrange the maraschino cherries in a decorative pattern across the surface. Return the assembled cake to the refrigerator for 1-2 hours before serving to allow all layers to meld together and achieve the perfect chilled consistency.