Preheat the oven to 350°F (175°C). Line an 8×8-inch baking pan with parchment paper and spray with non-stick cooking spray.
Make the Shortbread Crust: In a large bowl, cream together the cold butter, granulated sugar, and salt until light and fluffy. Add the vanilla extract (if using) and mix. Gradually add the flour and mix until the dough becomes crumbly. Press about 3 cups of the dough into the prepared pan and bake for 12-14 minutes, or until golden. Remove and set aside.
Prepare the Cherry Filling: If using homemade cherry pie filling, prepare it according to your recipe. If using canned, spoon the filling over the baked crust evenly.
Prepare the Crisp Topping: In a bowl, combine brown sugar, granulated sugar, flour, cinnamon, and salt. Add the cold butter cubes and use a pastry cutter or two knives to cut the butter into the mixture until it forms pea-sized crumbles. Sprinkle the crumble evenly over the cherry filling.
Bake in the oven for 30-35 minutes, or until the topping is golden brown. Remove from the oven and allow to cool completely.
Make the Glaze: In a small bowl, whisk together confectioners’ sugar, almond extract, and milk. Adjust milk for desired consistency. Drizzle the glaze over the cooled bars.
Slice into squares and serve.
