Preheat your oven to 350°F (175°C). Line two large baking sheets with parchment paper or silicone baking mats to prevent the cookies from sticking and ensure even browning.
In a large mixing bowl or the bowl of a stand mixer, cream together the softened butter, dark brown sugar, and granulated sugar. Beat on medium-high speed for about 2-3 minutes until the mixture is light and fluffy.
Add the egg, pure maple syrup, maple extract, and vanilla extract to the butter mixture. Continue to beat until well combined, scraping down the sides of the bowl as needed to ensure everything is incorporated.
In a separate medium bowl, whisk together the all-purpose flour, baking soda, salt, and ground cinnamon. This helps distribute the leavening agents evenly throughout the flour.
Gradually add the dry ingredients to the wet ingredients. Mix on low speed just until no streaks of flour remain. Do not overmix, as this can make the cookies tough. The dough should be soft but manageable.
Scoop rounded tablespoons of dough (about 1.5 to 2 tablespoons each) and place them 2 inches apart on the prepared baking sheets. Bake for 9 to 11 minutes, or until the edges are set and lightly golden, but the centers still look slightly soft.
Allow the cookies to cool on the baking sheet for 5 minutes. This allows them to firm up before you move them to a wire rack to cool completely.