Preheat the oven to 375 degrees.
Line a baking sheet with parchment paper.
Roll out the crescent sheet and cut into 8 squares. Place 1-2 inches apart on a baking sheet.
Mix cream cheese and sugar.
Add a spoonful of mixture to the center of each crescent square.
Add a heaping spoonful of cherry pie filling (about 3-4 cherries, plus the jelly) on top of the cream cheese mixture.
Fold up the corners of the crescent squares almost, but not quite to the center.
Bake for about 15 minutes, until slightly golden and dough is baked through.
Remove from oven, and allow to cool a bit.
Once cooled, mix the powdered sugar and milk.
Drizzle icing with a spoon, using a back and forth motion, across the pastries.