Preheat your oven to 350°F (175°C) and prepare your baking sheets by lining them with parchment paper.

In a large mixing bowl, combine the softened unsalted butter and packed brown sugar. Beat on medium speed for about 2–3 minutes until light and fluffy.

Incorporate pure maple syrup, a large egg, and vanilla extract into the mixture. Mix on low speed until well combined.

In a separate bowl, whisk together all-purpose flour, baking soda, salt, and ground cinnamon. Gradually add to the wet ingredients, stirring on low speed until just combined.

Using a cookie scoop or tablespoon, portion the dough into 1½-inch balls and place on prepared baking sheets, leaving space between each cookie.

Flatten each ball with your palm to create a disk shape.

Bake for 8–10 minutes until the edges are golden brown and centers are set but still soft.

Let the cookies cool on the baking sheets for a few minutes, then transfer to a wire rack to cool completely.

Whisk together the powdered sugar, maple syrup, and milk until smooth to make the glaze.

Drizzle the maple glaze over each cooled cookie.