Bake the Cake

Preheat oven to 350°F (175°C). Grease a 9x13-inch baking dish.

In a large mixing bowl, whisk together the chocolate cake mix, milk, vegetable oil, eggs, and vanilla extract until smooth.

Gently fold in ½ cup of the cherry pie filling.

Pour the batter into the prepared baking dish and spread evenly.

Bake for 30-35 minutes, or until a toothpick inserted in the center comes out clean.

Let the cake cool completely before assembling.

Prepare the Chocolate Ganache

Heat the heavy cream in a small saucepan over medium heat until steaming (but not boiling).

Pour the hot cream over the chocolate chips in a heatproof bowl. Let sit for 2 minutes, then stir until smooth and glossy.

Make the Whipped Topping

In a cold mixing bowl, beat the heavy whipping cream, powdered sugar, and vanilla extract until stiff peaks form.

Assemble & Serve

Spread the remaining cherry pie filling evenly over the cooled cake.

Pour the chocolate ganache over the top, spreading it evenly. Let set for about 10 minutes.

Spread the whipped topping over the ganache layer.