Preheat your oven to 375°F (190°C). Grab a standard muffin tin and give the inside of each cup a light spritz with nonstick cooking spray.
Unroll the tubes of crescent roll dough. Carefully place each individual triangle piece into the cups of your prepared muffin tin. Gently press the widest part of the triangle into the bottom of the cup, letting the point drape up the sides to form a little dough cup.
Using a spoon, carefully spoon 3 to 4 heaping tablespoons of cherry pie filling into each crescent roll cup. Leave a little room at the top so you can close them.
Take the points of the crescent roll dough hanging over the edge and gently fold them over the filling. Press the edges together as best you can to try and enclose the filling. They won't be completely sealed, and that's fine.
Pop the muffin tin into your preheated oven. Bake for about 13-14 minutes, or until golden brown and puffy. Carefully remove them from the oven.
While the cherry bites are still warm, make the glaze. In a small bowl, measure out your powdered sugar. Add 1 tablespoon of milk to start. Whisk it together until smooth. If it seems too thick, add another tablespoon of milk, a little at a time, whisking after each addition, until you get a nice, pourable glaze consistency.
Using a spoon, drizzle the glaze generously over the warm cherry bites right in the muffin tin. Let them cool in the tin for a few minutes before carefully removing them.
Serve them warm and enjoy!