1. Prepare the Oven and Muffin Tin: Setting the Stage for Baking

1. Preheat Oven: Preheat your oven to 350°F (175°C).
2. Prepare Muffin Tin: Generously spray a 24-cup mini muffin tin with non-stick cooking spray. This is crucial to prevent the cookie cups from sticking.

2. Prepare the Cookie Dough: Shaping the Cups

1. Divide Dough: Remove the refrigerated sugar cookie dough from its packaging. Divide the dough in half, and then cut each half into 12 equal slices. You should have 24 pieces of dough.
2. Roll into Balls: Roll each slice of cookie dough into a smooth ball.
3. Coat in Sugar: Place the granulated sugar in a small bowl. Roll each dough ball in the sugar until it’s evenly coated.

3. Place Dough in Muffin Tin: Creating the Cookie Cups

1. Arrange in Cups: Place each sugar-coated dough ball into a greased mini muffin cup.

4. Bake the Cookie Cups (First Bake): Forming the Base

1. Bake: Place the muffin tin in the preheated oven.
2. Baking Time: Bake for 15 minutes.
   • Check for Doneness: The cookie cups should be lightly golden brown around the edges.

5. Create Indentations: Making Room for the Filling

1. Remove from Oven: Carefully remove the muffin tin from the oven.
2. Press Centers: While the cookie cups are still hot, use the back of a small spoon, the handle of a wooden spoon, or your thumb to gently press down the center of each cookie cup, creating a small indentation or well. This will create space for the cherry pie filling.

6. Fill the Cookie Cups: Adding the Cherry Filling

1. Add Filling: Spoon about 1 tablespoon of cherry pie filling into the indentation of each cookie cup.
   • Tip: Don’t overfill the cups, or the filling may spill over during baking.

7. Bake Again (Second Bake): Setting the Filling

1. Return to Oven: Return the muffin tin to the oven.
2. Bake: Bake for an additional 3-5 minutes, or until the filling is heated through and bubbly.

8. Cool and Glaze (Optional): The Finishing Touches

1. Cool Slightly: Remove the muffin tin from the oven and let the Cherry Pie Cookie Cups cool in the tin for a few minutes before removing them.
2. Prepare Glaze (Optional): While the cookie cups are cooling, you can make the optional glaze. In a small bowl, whisk together the powdered sugar, melted butter, and milk until smooth. Add more milk, a teaspoon at a time, until the glaze reaches your desired consistency.
3. Drizzle with Glaze (Optional): Once the cookie cups have cooled slightly, drizzle the glaze over the tops.
4. Cool Completely: Let cool on wire rack.

9. Serve and Enjoy: Savoring Your Homemade Treat

1. Serve: Serve the Cherry Pie Cookie Cups warm or at room temperature.