Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper.
In a large bowl, beat the softened butter, granulated sugar, and brown sugar until light and fluffy, about 2 minutes.
Add the maple syrup, egg, vanilla, and maple extract. Mix until smooth.
The mixture may look slightly curdled—that’s okay.
In a separate bowl, whisk together the flour, cream of tartar, baking soda, salt, and cinnamon.
Add the dry ingredients to the wet and mix just until combined. Do not overmix.
In a small bowl, combine the rolling sugar and cinnamon. If using powdered sugar for extra crinkle, place it in a second small bowl.
Scoop the dough into 1 1/2-tablespoon balls.
Roll each ball in the cinnamon sugar. For bigger crinkles, roll again lightly in powdered sugar.
Arrange on the baking sheets, spacing 2 inches apart.
Bake for 9–11 minutes, until the edges are set and the tops have cracked. They should look slightly underbaked in the center.
Cool on the sheet for 5 minutes, then transfer to a wire rack to cool completely.
The centers will finish setting as they cool.