In a large mixing bowl, beat the cream cheese using an electric mixer until smooth and creamy. This should take about 1-2 minutes on medium speed.
Gradually add the cheesecake instant pudding mix to the cream cheese, mixing until well combined.
Pour in the vanilla extract and milk. Continue mixing until everything is smooth and creamy.
Gently fold in the Cool Whip (or homemade whipped cream) using a spatula. Be careful not to deflate the mixture; you want to keep it light and airy.
Stir in the cherry pie filling and mini marshmallows, ensuring they are evenly distributed throughout the fluff.
Add the pitted and halved cherries to the mixture, folding gently to combine.
Cover the bowl with plastic wrap or transfer the mixture to an airtight container. Refrigerate for at least 2 hours to allow the flavors to meld and the fluff to set.
Once chilled, give the fluff a gentle stir before serving. Spoon it into individual cups or a large serving bowl. Garnish with extra cherries and marshmallows on top for a beautiful presentation.