01 -
Spray a deep pie dish with non-stick cooking spray.
02 -
Pulse the shortbread cookies in a food processor until they reach a sand-like consistency. In a mixing bowl, mix the cookie crumbs with the melted butter until well combined. Press the mixture firmly into the bottom and up the sides of the prepared pie dish. Place the crust in the freezer while you make the filling.
03 -
Rinse out the food processor and add the peeled orange slices, orange zest, vanilla extract, and orange juice. Puree until smooth and set aside.
04 -
In a stand mixer (or a large mixing bowl with a hand mixer), combine 8 ounces of cream cheese and the orange Jello mix. Beat until smooth and well incorporated.
05 -
Fold in the sweetened condensed milk along with 8 ounces of Cool Whip until fully combined.
06 -
Beat the orange juice mixture into the filling until well blended.
07 -
Remove the crust from the freezer and pour the filling into it, smoothing the top with a spatula.
08 -
Refrigerate the pie for at least 2 hours for a soft-serve texture, or freeze for about 1 hour for a more frozen dessert consistency.
09 -
In a mixing bowl, whip the remaining 4 ounces of cream cheese and 4 ounces of Cool Whip together until smooth.
10 -
Spread or pipe the cream cheese whipped topping over the chilled pie and garnish with fresh orange slices. Serve cold or frozen, depending on your preference.