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Preheat your oven to 375°F (190°C). Lightly grease a standard muffin tin with nonstick cooking spray.
Unroll the crescent roll dough and place each piece into a muffin tin, ensuring the widest part of each dough triangle is at the bottom.
Spoon cherry pie filling into each dough cup, using about 3 to 4 heaping tablespoons per cup.
Gently fold the corners of the dough over the cherry filling to enclose it as much as possible. Bake for 13-14 minutes, or until golden brown.
While the cherry bites are baking, whisk together powdered sugar and milk in a small bowl until smooth.
Once the cherry bites are done baking, allow them to cool slightly and drizzle the prepared glaze over them.