1 box chocolate cake mix
1/4 cup cocoa powder
1 cup water
1/2 cup vegetable oil
3 large eggs
1 3.4-ounce package instant cheesecake pudding
1 cup milk
3/4 cup heavy whipping cream
3 Tablespoons powdered sugar
2 1/4 cups heavy whipping cream
1/3 cup cocoa powder
1/2 cup, plus 3 Tablespoons powdered sugar
1/2 teaspoon vanilla extract
For the Cake
Preheat oven to 350 degrees F. Line a cupcake pan with 24 cupcake liners.
In a medium-sized bowl, combine the cake mix, cocoa powder, water, vegetable oil and eggs. Beat on medium-high speed until all ingredients are well blended.
Add the can of cherry fruit filling and continue mixing until the ingredients are well incorporated. Use a spatula to mix the batter from the bottom of the bowl to the top to ensure it's well mixed.
Divide the batter evenly, filling each liner about 2/3 full and bake for 15-18 minutes until cupcakes are set.
Test the cupcakes for doneness by inserting a toothpick into the center. If the toothpick comes out clean, the cupcakes are done. Allow the cupcakes to cool completely.
For the Filling
In a medium sized bowl, combine the pudding mix and the milk and whisk just until the pudding mix starts to dissolve. Refrigerate until the pudding is completely firm.
Prepare the whipped cream: Put the bowl and whisk attachment in the freezer for 5-10 minutes to get them really cold (this step is optional, but a common practice). Pour the heavy whipping cream into the chilled bowl and beat until stiff peaks form.
Add powdered sugar and increase speed to medium high. Beat until stiff peaks form.
Remove pudding from refrigerator (after it has set) and gently fold in whipped cream until it's well combined. Place the filling in a Ziploc bag or piping bag. Keep in refrigerator until ready to use.
To assemble the cupcakes, remove the middle of the cupcake using a spoon, knife or cupcake corer.
Cut off the tip of Ziploc bag or use piping bag to fill center of cupcake with cheesecake mousse filling.
For the Topping
To make the chocolate whipped cream, prepare your mixing bowl as directed above by placing in freezer 5-10 minutes.
Pour the heavy whipping cream into the chilled bowl and beat until soft peaks form.
Turn the mixer off and first add the cocoa powder, then slowly mix into the whipped cream. Next add the powdered sugar and vanilla extract slowly and increase mixing speed to high and continue beating until stiff peaks form.
Use a large piping bag fitted with an open star tip and pipe the whipped cream on the cupcakes and serve. NOTE: These cupcakes must be refrigerated.