Cake:
Preheat oven to 350°F. Grease and flour a 9×13-inch baking pan; set aside.
In a large mixing bowl, stir together the dry ingredients; set aside.
In a separate bowl, mix together buttermilk, oil, eggs and vanilla extract until the mixture is smooth and thick. Pour batter into the prepared pan and bake for 28 to 32 minutes, until the top is golden brown. Test doneness by inserting a toothpick in the center of the cake — if it comes out clean, it’s done. Allow cake to cool for 15 minutes.
Meanwhile, in a medium bowl, stir together the Jell-O powder and boiling water until dissolved, about 2 minutes. Stir in the cold water.
Using a wooden skewer, poke holes all over the cake. Evenly pour the Jell-O mixture over the cake. Refrigerate for at least 3 hours.
Whipped White Chocolate Cream Topping:
Place a large mixing bowl (preferably stainless steel) in the freezer while the cake chills. Once chilled, pour the whipping cream into the cold bowl.
Using a hand mixer, whip the cream until soft peaks form. Add powdered sugar and extract, then continue mixing on high until just before stiff peaks form.
Add the pudding mix and reduce to low speed. Continue mixing until thickened, scraping the bowl as needed.
Check the bottom of the bowl to ensure pudding mix hasn’t clumped. If the mixture is too thick, add milk 1 tsp. at a time until desired consistency is reached.
Frost the chilled cake with whipped topping. Return to the refrigerator for at least 1 hour.
Serve with cherry pie filling or fresh cherries.