- Preheat the oven to 325 degrees and spray a deep 9x13 cake pan with nonstick cooking spray. Set aside. 
- In a large mixing bowl, combine the two cake mixes, eggs, oil, milk, and 1 cup of cold water. Using a hand mixer or stand mixer, beat until no lumps appear. It will seem thin, but this is what you want. 
- Pour into your prepared cake pan and bake for 50-60 minutes or until a toothpick inserted into the middle of the cake (deeper than just the top bit of cake) comes out clean. Let cool for about 20 minutes. 
- With the handle of a wooden spoon, or with a similarly shaped object, poke holes in the cake. There should be a hole about every inch and be careful to not go all the way through the cake. Just go a little over halfway through with the holes. 
- Pour jello mix in a medium mixing bowl and add in boiling water. Stir until jello is dissolved. Place jello in a pourable container. 
- Slowly pour jello over the top of the cake, first covering the holes and then any surface of the cake left after that. 
- Place cake in fridge, covered with plastic wrap, for 4 hours or until the jello is set. 
- To prepare the frosting, place cranberry sauce in a medium mixing bowl and use a fork or other utensil to break it up until no large chunks remain and it resembles a homemade style cranberry sauce. 
- Add cool whip to the bowl with the cranberry sauce and fold it together until fully combined. 
- Frost the top of the cake with the mixture. Slice, serve, and enjoy!