Preheat oven to 350 degrees. Line a 13x9 inch baking pan with parchment paper or lightly spray with cooking spray.
To prepare the shortbread mix, the flour, 1/4 cup of brown sugar, baking powder, 1 tablespoon maple syrup and salt in a large bowl. Add 1/2 cup of the butter and using a pastry blender or fork, combine the mixture well until it resembles coarse meal. Press the mixture evenly into the bottom of the prepared baking dish. Bake in the preheated oven until lightly browned about 15-20 minutes. Sprinkle the crumbled bacon in an even layer over the shortbread crust.
To prepare the maple glaze, melt the remaining 1/2 cup of butter over medium heat in a medium sized saucepan. Whisk in the remaining 2 tablespoons of maple syrup, the confectioner’s sugar, the remaining brown sugar and the vanilla until smooth. Bring to a boil, stirring constantly. Let boil for one minute.
Pour the glaze over the bacon and shortbread crust, spreading with a spatula or knife. Allow to cool to room temperature before cutting into squares.