Preheat the oven to 350° and line 2 cookie sheets with parchment paper.
Combine the 1/4 cup granulated sugar and 2 teaspoons cinnamon in a small bowl to make cinnamon sugar mixture for rolling. Set aside.
In a large bowl, combine butter, brown sugar, and granulated sugar and stir until completely combined.
Add in egg, egg yolk, and vanilla and mix well.
Add the flour, cream of tartar, salt, baking soda, and cinnamon and mix until fully combined.
Using 1/2 cup measuring cup, portion the dough into balls. It should make 6 even-size balls.
Roll each ball of dough between your palm to smooth then roll it in the cinnamon sugar mixture.
Place 3 cookies on each cookie sheet, evenly spaced so they room to spread.
Bake, one sheet at a time, for 16-19 minutes. 16 minutes will result in chewy cookies and 19 will result in a little crisper cookie.
Let cool on the cookie sheet for 5-10 minutes before moving to a cooling rack.