Preheat oven to 350°F. Spray a 9×13” pan with cooking spray.: When you preheat, you should smell the faint warmth of the oven as it reaches 350°F , a signal that the baking environment is ready. Spraying the pan ensures the baked cake releases cleanly, preserving the soft edges and glossy top. A cold pan or underheated oven can lead to uneven rise and a denser crumb, so wait until the temperature is stable before popping the batter in. If your bake seems uneven, rotate the pan halfway through the bake time to promote even coloring. Don't skip the spray, because sticking will make it hard to poke holes uniformly later.
Add all cake ingredients to a large bowl and mix, according to package directions, until smooth, about 2 minutes. Bake for 25-35 minutes, until a toothpick comes out clean. Remove from oven and let cool to room temperature before topping.: As you mix, watch the batter transform from lumpy to silky, and you should smell cocoa lifting as air is incorporated. A smooth batter leads to an even bake and tender crumb that soaks well. The bake time window lets the center set without drying the edges; the toothpick should come out with a few moist crumbs but not raw batter. When it emerges clean, you will notice a gentle pullback from the pan edges and a uniformly domed top. Cooling to room temperature is critical because warm cake will cause the fillings to run, losing the poked-pocket effect. A common mistake is rushing the cooling; that makes the fillings sink and spread instead of settling into pockets.
In a small bowl, stir together sweetened condensed milk and 1/4 cup Cherry Coke.: The mixture will glisten and become slightly thinner than straight sweetened condensed milk , with a faint cola aroma. Stir until the liquids integrate smoothly, no streaks of thick milk remaining. This thinner syrup is key for seeping into the holes without creating a soggy mess. If it seems too thick, add a teaspoon of the soda at a time to reach a pourable consistency. Avoid overheating or whipping it, which can change the texture and make it less likely to penetrate the crumb.
In another small bowl, heat hot fudge until liquid, but not too hot. Stir in remaining 1/4 cup of Cherry Coke.: Warm hot fudge until it loosens and gives off a rich chocolate scent, stirring so it becomes glossy and smooth. Incorporating the soda thins it slightly and layers in that cola note. The temperature should be warm to the touch, not scalding, to prevent melting the top layers later. If the fudge is overheated it can become grainy and separate, so heat gently in short bursts and stir frequently. Keep a spoon handy to test thickness, you want it pourable but not runny.
Poke several holes in the top using the handle of a wooden spoon.: You will hear a soft tapping as the handle punctures the crumb and feel gentle resistance as you push to a consistent depth, creating wells for the syrups. Space the holes evenly across the surface so the liquids distribute uniformly. The holes should be deep enough to reach the lower third of the cake, so the fillings sink into the body rather than staying on top. A common pitfall is poking too shallowly, which prevents the syrup from soaking through; conversely, overly large holes can cause structural collapse when fillings are added. Maintain steady pressure for uniform wells.
Pour the sweetened condensed milk mixture evenly over the top, being sure to get it in the holes.: As you pour, you will see the glossy liquid pool and tug into the wells, creating shiny dark spots across the cake. Use a ladle or measuring cup for control, and pour slowly so the syrup has time to sink. The sound is almost silent, but visually you can watch the syrup vanish into the crumb, indicating it is doing its job. If you pour too quickly it will run off the sides and leave sections dry, so take your time and cover every area evenly.
Do the same with the hot fudge mixture.: The warmed, glossy hot fudge will create richer, chocolatey pockets that contrast with the sweetened condensed milk. Pour in a controlled pattern over the same wells to layer flavors. The warm fudge will sink slightly but remain more concentrated, providing depth in each bite. If the fudge is too hot it can melt the underlying creaminess, and if too cool it will sit on top and not penetrate. Aim for a sensual pour that leaves ribbons of shiny chocolate across the surface.
Spread cherry pie filling over the top of the cake. Spread Cool Whip evenly over cake, cover with plastic wrap and chill for several hours before serving.: Spoon the cherry pie filling across the top so ruby globs create joyful contrast. The filling adds bright tartness and visual appeal, with a slight syrup that mingles with the underlying layers. Smoothing Cool Whip on top creates a cloud like layer that balances the dense, soaked cake underneath. Covering and chilling lets the flavors meld and the textures firm up; you will notice the syrup set and the cake become sliceable. A common mistake is serving too soon; insufficient chilling results in a runny, unstable dessert, so give it at least four hours for best results.
Top with sprinkles before serving, if desired.: A sprinkle or two adds nostalgia and a subtle crunch against the soft Cool Whip top, and visually it signals a celebration. Add them just before serving so they keep their color and crunch. If you add them too early they can bleed color into the topping or lose their snap. Keep extras nearby for guests who like more decoration.