Preheat oven to 375°F. Lightly grease a 24-cup mini muffin tin.
Beat cream cheese, granulated sugar, and vanilla until smooth and fluffy.
Unroll crescent dough. Pinch seams closed, then cut into 24 even squares.
Press one dough square into each muffin cup, creating a small well.
Spoon about 1 teaspoon cream cheese mixture into each well.
Top with a cherry and a little syrup from the filling.
Brush exposed dough with melted butter. Sprinkle cinnamon and coarse sugar if using.
Bake until puffed and golden, 12–14 minutes.
Cool 10 minutes in the pan. Loosen edges and transfer to a rack.
Whisk powdered sugar with milk until smooth. Drizzle over warm bites and serve.