Prep. Spray a deep pie dish with no-stick spray.
Make the crust. Pulse the cookies in a food processor until they reach a sand-like consistency. In a mixing bowl, mix the cookie crumbs with the melted butter and then press the mixture into the bottom and up the sides of the pie dish. Pop it in the freezer while you make the filling.
Create orange flavor. Rinse out the food processor and add the orange slices, orange zest, vanilla extract, and orange juice. Puree until smooth. Set aside.
Make the filling base. In a stand mixer (a large mixing bowl and a hand mixer will also work), combine 8 ounces of cream cheese and the Jello mix. Beat until smooth.
Make it fluffy. Fold in the sweetened condensed milk along with 8 ounces of Cool Whip.
Put it all together. beat the orange juice mixture into the filling.
Assemble the pie. Pour the filling into the pie crust.
Chill. Chill the pie in the fridge for a couple of hours for a soft-serve texture or pop it in the freezer for an hour for a more frozen dessert.
Make the topping. Whip the remaining cream cheese and cool whip together until smooth.
Garnish. Top the pie with the cream cheese whipped cream and orange slices.