Preheat the oven to 350º Fahrenheit and grease a 9x13 inch baking dish with cooking spray.
In a large mixing bowl beat together the cake mix, eggs, 1 ½ cups of heavy cream and vegetable oil with a hand or stand mixer until fully smooth. Scrape the sides of the bowl with a rubber spatula as needed
Spread the cake batter into the prepared baking pan and bake for 30-35 minutes or until the top bounces back when gently tapped or a toothpick comes out of the middle of the cake with only a few crumbs. Do not overbake.
Remove the cake from the oven and let it cool for 20 minutes.
Make the jello syrup:
Once the cake has cooled for 20 minutes, poke several large holes all over it with the bottom of a stirring spoon. Do not poke all the way to the bottom of the cake, only poke about ¾ of the way down.
Pour the strawberry gelatin powder into a medium bowl and whisk in the boiling water until dissolved.
Gradually add in the remaining 1 cup of heavy cream, whisking constantly, until it is all added and combined. You should have a dark pink, creamy liquid.
Pour the strawberry gelatin mixture mixture over the cake slowly, being sure to fill the holes as much as possible and avoiding the edges of the cake.
Spread any remaining liquid sitting on the top of the cake into the holes.
Cover well and place in the refrigerator for 2-4 hours or overnight.
Frost the cake:
When ready to cut and serve the cake, remove from the refrigerator, uncover and spread the whipped topping all over the top.
Make the strawberry crunch crumbles:
Place 20 of the cookies in a food processor and pulse 1-2 times to begin to crush them.
Add in the strawberry jam and pulse several more times until the cookies are roughly crumbled and the syrup is mixed in.
Remove half of the cookie crumbs and set aside (it should be about 1 1/2 cups removed and 1 1/2 cups left in the food processor.)
To the crumbs in the food processor, add the box of strawberry jello powder and the heavy cream. Close the food processor and pulse until you have pink coarse crumbs.
Add the white cookie crumbs back in to the food processor. Add the remaining 5 Oreo cookies. Pulse 2-3 times to blend the mixture. You should have a nice mix of strawberry and vanilla crumbles.
Sprinkle the topping evenly over the whipped topping, spreading gently if necessary to reach all the edges, and then cut and serve. Garnish with fresh strawberries and whipped topping, optional.
Store this cake covered in the refrigerator until serving.
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Notes
Refer to the article above for more tips and tricks.
The calories shown are based on the cake being cut into 15 pieces, with 1 serving being 1 slice of cake. Since different brands of ingredients have different nutritional information, the calories shown are just an estimate. **We are not dietitians and recommend you seek a nutritionist for exact nutritional information. The information in the nutrition box are calculated through a program and there is room for error. If you need an accurate count, I recommend running the ingredients through your favorite nutrition calculator.**