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To a medium bowl or measuring cup, add milk and instant vanilla pudding and whisk together until incorporated. Set aside so it will set up a bit before pouring.
Open the Cookie Tin and remove the papers. Leave the cookies in the tin and pour egg nog evenly over the cookies. Let the cookies soak up the egg nog for about 5 minutes.
Next, use a potato masher or ground beef masher to crunch up the cookies in the tin into large pieces. Don’t break them up too much, just into bite size pieces.
Now evenly pour the milk/vanilla pudding mixture over the eggnog soaked crushed cookies. Let it settle into the cookie layer.
Next, spoon the cherry pie filling over the cookies in an even layer.
Cover with lid and place it in the refrigerator. (This step is important because it helps the pudding to fully set up, allows the flavors to meld together and makes the dessert very cold. Chill for at least 1 hour)
Top with Cool Whip and sprinkles before serving, spoon out individual portions into bowls and enjoy!