Preheat the oven to 350°F. Spray a 9x13 baking dish with nonstick cooking spray.
In a large bowl, mix together the dry ingredients: flour, brown sugar, baking soda, and cocoa.
Cut the cold butter into small pieces with a knife.
Add the chopped butter to the bowl of dry ingredients. Use a pastry cutter, fork or your fingers to mix in the butter and break apart until it's crumbly and pea-size in shape.
In a separate bowl mix together 1 egg and vanilla extract.
Pour into dry mixture and mix together.
Slowly add the milk 2-3 Tbsp at a time until the batter is wet enough to stick together. Reserve 1 cup of the cookie base for the topping.
Add the cookie base to greased baking dish. Press firmly into the bottom. Spread the cherry pie filling on top.
Add the reserved 1 cup cookie base and chocolate chips to a bowl. Mix together.
Sprinkle onto the top of the dessert. Bake for 30-35 minutes. Let cool completely at room temperature. Cover and place in the fridge to chill for 2 hours.
Once chilled, slice into squares. Use a spatula to remove from the pan, serve and enjoy!
Recipe Notes:
Use cold butter! It cannot be room temperature. Chop the butter into small pieces, then use a pastry cutter, fork or just your fingertips to break it apart into even smaller pieces. This the key to the perfect consistency. Crumbly butter in the dry flour mixture will create the perfect cookie crumb base.
Grease the baking dish really well. Use nonstick cooking spray to make sure the entire pan is coated. This will make it much easier to remove after chilling in the fridge.
Use a flimsy rubber spatula to help release the bottom of the dessert from the pan. These are my absolute favorite kitchen tools for a variety of purposes. The key is that they must be bendable and not the stiff versions.
If you love cherry pie filling, you could add more! I felt like this recipe could’ve used 1 ½ cups and plan to try it that way next time I make it.
If you don’t like cherry pie filling, you can replace it with jam, jelly or homemade strawberry sauce. Any other pie filling flavors would probably also work (apple, rhubarb, strawberry, raspberry, cranberry or blueberry).