Spray a 9×13-inch pan with non-stick cooking spray and set aside.
Makek the cake:
Combine the box of cake mix with ingredients (make according to package directions).
Pour batter into the prepared baking pan smooth into an even layer.
Bake for 25-30 minutes or until a toothpick inserted in the center comes out clean.
Cool the cake completely, for about 1 hour.
Poke and fill cake:
Use the handle of a wooden spoon to poke holes over each inch of the cake. Make about 80 holes (8 across by 10 rows). Set aside.
In a small bowl, mix the jello with the boiling water. Pour jello over the cake, allowing the jello to run down into the holes of the cake.
In a large bowl, whisk the vanilla pudding with the milk just until it begins to thicken.
Pour the cold heavy whipping cream into a cold medium mixing bowl and whip the cream on high speed until medium to stiff peaks form, about 1 minute. Make sure it is thick.
Add powdered sugar and vanilla. Whip another 20 second. Add to the pudding and gently mix.
Mash ¾ cup of raspberries with a fork and add to the pudding/whipped cream mixture. Gently stir.
Spread evenly over the chilled cake.
Garnish the cake with remaining raspberries. Refrigerate at least 3 hours before serving.