Preheat the oven to 325ºF (177ºC) and prepare a 9x13 baking pan by spraying the sides with cooking spray and fitting the bottom with parchment paper.

Place all of the dry ingredients into the bowl of a stand mixer and stir on low for 30 seconds to fully combine them. Add the vegetable oil, eggs, vanilla, and buttermilk and mix on low until just combined. With the mixer still on low, add the hot coffee (or hot water) in a slow stream, then turn the mixer to medium and beat until smooth, about 2 minutes. The batter will be very thin.

Pour into the prepared cake pan and bake for 30-35 minutes, until a toothpick inserted comes out clean. Cool completely before adding the toppings.

Add all of the cherry filling ingredients into a medium saucepan set over medium heat. Stir to combine and bring to a boil, stirring occasionally. Reduce the heat to a simmer and continue cooking the cherry mixture for 5 minutes.

Using a mesh strainer or slotted spoon, remove the cherries from the saucepan and place them into a separate container to cool. This will be your cherry filling.

Continue cooking the liquid that remains in the saucepan, stirring frequently until it reduces by half, about 10 minutes. Pour the liquid into a separate container to cool and set aside. This will be your cherry syrup.

Make the stabilized whipped cream right before you're ready to assemble the cake. Get started by chilling the metal bowl of your stand mixer for 15-20 minutes in the refrigerator or freezer.

Sprinkle the gelatin into a small glass measuring cup or microwave safe dish. Add the cold water and whisk until the gelatin is dissolved. Set the mixture aside for 5 minutes to let the gelatin set.

While the gelatin is setting, add the heavy whipping cream, powdered sugar, and vanilla extract into the chilled metal bowl of your stand mixer fitted with the paddle attachment and mix on low speed to combine. Turn the mixer to high speed and beat until the mixture is thickened, stopping just shy of reaching soft peaks, about 1 min.

At this point, the gelatin should be solidified. If so, pop it into the microwave for 5-10 seconds, until the mixture has re-liquified but is still cool to the touch. Use a whisk to briefly stir the gelatin mixture together to make sure it's smooth.

With the mixer on low speed, drizzle the liquid gelatin into the cream. Slowly increase the speed to medium-high and continue to beat until you have reached stiff, fluffy peaks, about 2 minutes. Use immediately to ensure the best consistency for piping.

Place the chocolate chips into a heat resistant bowl and set aside. In a saucepan over medium-high heat, warm the heavy whipping cream until it just starts to simmer. When it's reached this point, pour the cream into your bowl of chocolate and let sit for about 30 seconds.

Whisk the chocolate and cream together until it’s uniform in consistency and there are no bits of chocolate left on your whisk. Cool the ganache at room temperature for 10-20 minutes, or until the ganache itself is room temperature or slightly above, before drizzling the cake.

Transfer the cooled chocolate cake onto a serving plate (upside down so you can peel off the parchment paper lining). Use a pastry brush to add all of the cherry syrup onto the cake as a soak.

Add a thin layer of whipped cream frosting onto the cake layer and create a slight dam on the outer edges. Add all of the cherry filling into the dam. Top with the rest of the whipped cream frosting and use an angled spatula to frost swirls and rustic texture onto the surface of the cake.

Drizzle the ganache onto the surface of the cake diagonally in one direction, then diagonally in the opposite direction. Place fresh cherries around the edges of the cake and serve, or store in the refrigerator until ready to serve.