Preheat the oven to 375℉. Lightly spray a mini muffin pan with nonstick cooking spray.
Lay out thawed puff pastry sheets side by side. I like to roll mine a little flatter with a rolling pin to get rid of any kinks and make sure the sides are even.
Cut each sheet into 4 rows by 4 rows to get 16 squares from each sheet. Press each square of puff pastry into each tin. Set aside.
In a medium bowl, use a hand mixer to mix cream cheese, sugar, and vanilla.
Spoon about 1 teaspoon of cream cheese mixture into each puff pastry square. Top with about ½ tablespoon of cherry pie filling.
Bake in the oven for 18-22 minutes until the puff pastry is golden brown. Remove from the oven and cool on a wire rack.
Icing, optional
In a small bowl, whisk together powdered sugar and milk until runny. Drizzle over the top of cooled cherry cheesecake bites.