In a large mixing bowl, whisk together pudding mixes and milk until well combined.
Add peppermint extract and whisk to combine.
Add a generous amount of red food coloring and whisk to incorporate.
Add about 1 cup of the whipped topping and whisk to combine. If needed, you can add a bit more red food coloring at this point to get your desired shade for the pie filling.
Pour the filling into your premade Oreo crust.
Cover and move to the refrigerator to chill for at least 4 hours.
Before serving, add the remaining whipped topping to a piping bag fitted with a 1M open star tip.
Add single squeezes of the whipped topping all the way around the outer edge of the pie.
Inside of your whipped topping border, sprinkle crushed candy canes.
Notes
Storage: Store covered in the refrigerator for up to 4 days.