First, make the cinnamon sugar mixture. Combine the brown sugar and cinnamon in a small bowl and stir to combine. Set aside.
In a stand mixer fit the paddle attachment, beat the butter and brown sugar sugar together until light and airy, about 2 minutes.
Use a rubber spatula to scrape down the sides of the bowl and add the maple syrup, egg, vanilla extract and maple extract if using. Beat until smooth and fluffy, about 2 minutes.
Add the flour, baking powder, baking soda and salt. Mix on low speed, gradually increasing to high. Mix until no streaks of flour remain. Do not over mix.
Add the brown sugar cinnamon mixture to the mixing bowl and fold the mixture one or two times to mix in the sugar a little bit–you don’t want to over mix it. You want the cinnamon sugar to stay mostly separate from the cookie so you get nice big swirls!
In a separate bowl, combine all the ingredients for the streusel topping and use a fork to mixture until crumbly and clumping together.
Use a 1.5 ounce cookie scoop to scoop out the dough onto your prepared baking sheet. Lightly flatten the top of cookie dough balls so that the streusel has a flat surface to stick to. Top with a heaping spoonful of the streusel topping, really pressing it into the dough.
Bake the cookies for 12 to 15 minutes or until the edges are set, but the centers are still a little doughy. Allow to cool completely before eating!