In a medium-sized bowl, add the jello and carefully pour in the boiling water. Using a whisk, stir until dissolved. Set aside to cool, about 20 minutes.
In a large bowl, add the softened cream cheese and crushed pineapple. Using a hand mixer on low speed, mix together the cream cheese and pineapple, gradually increasing the mixer speed to medium-high. Mix together for about one minute until fully combined. There may be small flecks of cream cheese, and that’s okay.
Pour the cooled jello liquid into the cream cheese and pineapple mixture. Using the hand mixer, start on low speed so it doesn’t splash around a lot and begin to mix, gradually increasing the speed to medium until it is well-combined.
Add the 12 ounces of Cool Whip. Begin with a low speed on a hand mixer and gradually increase the speed to medium-high until well-combined, about two minutes. It will still be in liquid form but trust the jello to do its work and it will solidify as it chills.
Pour into a large glass serving bowl, cover with cling wrap and chill for at least four hours or until ready to serve. You can also use a 9x13 pan as an option instead.
Serve with a dollop of Cool Whip and fresh berries or other fruit as garnish if desired.