Line 2 cookie sheets with parchment paper or silicone baking mats. Set aside.
In a large bowl, whisk together the flour, salt, baking soda, baking powder, and cinnamon. Set aside.
2 2/3 cups all purpose flour, spooned and leveled, 1 tsp. salt, 1 tsp. baking soda, 1/2 tsp. baking powder, 1/2 tsp. ground cinnamon
In a stand mixer fitted with the paddle attachment, cream together the cold cubed butter and brown sugar for 3-4 minutes. Start off on low speed, then you can increase the speed to medium once the butter is incorporated into the sugar.
12 Tbsp. salted butter, cold and cut into cubes, 1 1/4 cups dark brown sugar, packed
Add in the egg yolk, maple syrup and extract until combined. Scrape down the sides of the bowl as needed.
1 large egg yolk, 1/3 cup pure maple syrup, 2 tsp. vanilla extract (or 1 tsp. maple extract and 1 tsp. vanilla for more maple flavor)
Gradually add in the dry ingredients on medium-low speed and mix just until combined. If the cookie dough looks or feels dry you can add a splash of milk and mix it in to help hydrate the dough.
Using a 2 Tbsp. cookie scoop, scoop the dough and drop onto a plate or baking sheet (be sure there is room in the fridge if using a baking sheet).
Chill the scooped dough balls for 30 minutes – 1 hour or up to overnight.
Mix the granulated sugar and cinnamon in a small dish.
3 Tbsp. sugar, 1/2 tsp. ground cinnamon
Preheat the oven to 350°F. Drop the chilled cookie dough balls in the cinnamon sugar mixture, tossing to coat all sides. Place on the prepared baking sheet.
Bake for 10 minutes. Cookies will be very soft and puffy at first, allow to cool on the pan for an additional 10 minutes, then move to a cooling rack to cool completely.
Microwave the butter and maple syrup in a microwave safe bowl until melted. Then whisk in the powdered sugar, vanilla extract and pinch of salt until smooth. Adjust powdered sugar as needed to get a good glaze consistency.
2 Tbsp. salted butter, 1/4 cup + 1 Tbsp. pure maple syrup, 3/4 cup powdered sugar, 1/2 tsp. vanilla extract, pinch of salt
Drizzle on top of cooled cookies and enjoy!