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, combine the cookie crumbs with the melted butter, then press the mixture into the bottom and up the sides of the pie dish. Place in the freezer while preparing the filling.
03 -
Rinse the food processor and add the orange slices, orange zest, vanilla extract, and orange juice. Puree until smooth and set aside.
04 -
In a stand mixer (or large mixing bowl with hand mixer), combine 8 ounces of cream cheese and the Jello mix. Beat until completely smooth.
05 -
Fold in the sweetened condensed milk and 8 ounces of Cool Whip until fully incorporated.
06 -
Beat the orange juice mixture into the filling until well combined.
07 -
Pour the filling into the chilled pie crust, spreading evenly to the edges.
08 -
Refrigerate the pie for two hours for a soft-serve texture, or freeze for one hour for a firmer, more frozen dessert consistency.
09 -
Whip the remaining 4 ounces of cream cheese and 4 ounces of cool whip together until smooth and fluffy.
10 -
Top the chilled pie with the cream cheese whipped topping and decorative orange slices before serving.