Preheat the oven to a temperature of 375°F.

Prepare a standard muffin tin by applying a layer of nonstick cooking spray.

Carefully unroll the crescent roll dough and position individual pieces into the respective sections of the muffin tin, ensuring that the wider section of the dough is placed at the bottom.

Precisely add the cherry pie filling to each portion of the crescent roll dough. Each section should receive approximately 3 to 4 tablespoons of filling. Ensure uniform distribution.

Proceed by methodically folding the dough over the filling, ensuring it encases the filling securely.

Bake the assembled pie bites in the preheated oven for a duration of approximately 13-14 minutes, or until they achieve a golden-brown hue.

In a separate mixing bowl, combine the powdered sugar and milk. Whisk the ingredients together until a smooth consistency is achieved.

Once the pie bites are sufficiently cooled, uniformly drizzle the prepared glaze over each bite.