Preheat oven to 350 degrees F. Line a 9x13 inch baking pan or 3 8-inch round cake pans with parchment paper and spray with non-stick spray.
In the bowl of your mixer combine the cake mix, mandarin oranges (with the juice), eggs, and oil. Mix until combined.
Pour the batter into the 9x13 inch baking pan OR divide equally between 3 8-inch round cake pans.
Place in oven and bake for 25-30 minutes or until a toothpick stuck in the center comes out clean.
Remove from oven and let cool completely.
While the cake cools make the frosting. In a large bowl combine Cool Whip, crushed pineapple (well drained!), and 1 3.5 ounce box of instant vanilla pudding. Stir until well mixed. Place in refrigerator until cake is ready to frost.
Once cake is fully cooled spread the frosting over the cake. If you made 3 round cakes you’ll frost the first round, then place the second round on top, add another layer of frosting and top with the final cake round. Use the remaining frosting to cover the entire outside of the cake.