Step 1: Bake the cake
Prepare and bake the chocolate cake according to the package directions in a 9×13-inch baking dish. Once baked, let it cool for about 10–15 minutes.

Step 2: Poke the cake
Using the handle of a wooden spoon or a thick straw, poke holes all over the surface of the warm cake, spacing about 1 inch apart.

Step 3: Pour the condensed milk
While the cake is still slightly warm, slowly pour the sweetened condensed milk over the entire surface, letting it soak into the holes.

Step 4: Spread the cherry filling
Gently spread the cherry pie filling over the top, making sure it gets into the holes as well. Add the almond extract into the cherry filling if using for an extra pop of flavor.

Step 5: Sprinkle the chocolate chips
While the cake is still slightly warm and sticky, sprinkle 1 cup of mini chocolate chips evenly over the top.

Step 6: Chill the cake
Refrigerate the cake for at least 1–2 hours, allowing everything to soak together and set properly.

Step 7: Frost with whipped topping
Once chilled, spread the whipped topping evenly over the entire cake.

Step 8: Garnish and serve
Sprinkle additional mini chocolate chips or shaved chocolate on top. Add maraschino cherries if desired. Slice and serve!