Spray a deep pie dish with nonstick spray. Set aside while you make the crust.

Pulse the shortbread cookies in a food processor until they resemble coarse sand. Transfer to a bowl and mix with melted butter until fully moistened.

Press the crust mixture into the bottom and up the sides of the pie dish. Use your fingers or a measuring cup to press it down evenly. Place the dish in the freezer to set while you make the filling.

Rinse out your food processor and add the peeled orange slices, zest, vanilla, and orange juice. Blend until completely smooth. Set the puree aside.

In a large mixing bowl or stand mixer, beat 8 ounces of cream cheese with the orange Jello powder. Beat until the mixture is smooth and creamy with no lumps.

Fold in the sweetened condensed milk and 8 ounces of Cool Whip. Mix gently until smooth and light.

Add the orange puree into the filling and beat again until everything is fully incorporated. You should have a fluffy, citrusy mixture that smells amazing.

Pour the filling into the prepared pie crust. Smooth the top with a spatula and tap the dish gently to remove any air bubbles.

Chill the pie in the refrigerator for at least 2 hours for a soft, creamy texture. For a firmer, frozen version, place in the freezer for about 1 hour.

In a small bowl, whip the remaining 4 ounces of cream cheese and Cool Whip until smooth. This creates a light cream topping.

Once the pie is fully set, spread or pipe the whipped cream mixture over the top. Garnish with fresh orange slices or extra zest for a fresh finish.