Gently split each Grands biscuit in half along the flaky layers (this will give you 16 pieces total). Roll out and flatten each piece into a small circle, about 3 to 4 inches wide. You want it flat enough to hold the filling but not too thin that it tears.
Spoon a small amount of cherry pie filling into the center of each dough round - about 2 to 3 cherries and a little bit of the syrup. Don’t overfill, or they’ll be hard to seal and might burst in the air fryer.
Carefully gather the edges of the dough up around the filling and pinch them closed at the top to seal. You’re aiming for a rough ball shape, with all the seams pinched together on top. It’s okay if they’re not perfect, just make sure they are sealed so the filling stays inside.
Lightly spray the air fryer basket with nonstick spray to prevent sticking. Place the sealed bites seam-side up in the basket, making sure they’re not touching. Depending on the size of your air fryer, you may need to cook in batches - mine fits 8 at a time comfortably.
Set your air fryer to 350°F. Cook the cherry pie bites for 5 minutes, then gently flip them over and cook for another 5 minutes. They should be golden brown and slightly crisp on the outside.
Remove the bites from the air fryer and let them cool for a few minutes on a wire rack or plate. While they’re cooling, mix together the powdered sugar and milk in a small bowl until you have a smooth glaze. Drizzle it over the warm cherry pie bites and let it set for a few minutes before serving.
Serve and enjoy.