Beat 8 ounces cream cheese, 1/4 cup powdered sugar, 2 teaspoons orange extract, and 8 drops orange Wilton Gel Food Color until completely smooth. The mixture should look glossy and evenly orange with no specks of unmixed cream cheese.
With the mixer running, pour the chilled gelatin into the orange cream cheese mixture in a slow stream, then refrigerate the bowl for 1 hour. After chilling, it should look thicker than before and hold soft swirls when stirred.
In a separate bowl, beat the remaining 8 ounces cream cheese with 1 cup confectioners' sugar and 1 teaspoon pure vanilla extract until smooth. The filling should be creamy, pale, and easy to spread with no gritty pockets.
Fold 1 cup Cool Whip into the vanilla cream cheese mixture until no white streaks remain. Keep the motion gentle so the mixture stays airy and light rather than dense.
Spread the cheesecake mixture over the frozen crust with an offset spatula, smoothing it all the way to the corners. The layer should sit evenly on top without picking up crumbs from the base.
Fold the remaining 2 cups Cool Whip into the chilled orange mixture until smooth and fully combined. The finished texture should be thick, fluffy, and velvety enough to mound lightly on the spatula before slowly settling.
Spread the orange cream over the cheesecake layer, then refrigerate the pan overnight or for at least 6 hours. Once set, the top should feel firm and cool with clean layers visible at the edges of the pan.