Preheat oven to 350°F (175°C) and lightly grease a 9×13-inch baking pan.
In a large mixing bowl, whisk together cake mix, eggs, oil, and water until smooth and lump-free.
Fold in mini chocolate chips gently to distribute evenly through the batter.
Pour batter into the greased pan and spread evenly.
Bake for 25–30 minutes, or until a toothpick inserted in the center comes out mostly clean. Cool for 10 minutes.
While the cake is still warm, use a toothpick or skewer to poke holes about 1 inch apart across the entire surface, roughly ½ inch deep.
If desired, mix almond extract into the cherry pie filling. Slowly spoon the filling over the cake, letting it seep into the holes and cover the top evenly.
Cover loosely with plastic wrap and refrigerate for at least 2 hours, or overnight for deeper flavor.
Chill your mixing bowl and beaters for 5–10 minutes before whipping the cream. Pour cold heavy cream into the bowl and beat on medium speed until foamy.
Increase speed to high, then add powdered sugar and vanilla extract. Continue beating until stiff peaks form.
Spread whipped cream over the chilled cake evenly. Create soft swirls for a decorative touch.
Top with fresh or maraschino cherries just before serving.
Slice, serve chilled, and enjoy the layers of flavor in every bite.