Making The Sugar Cookie Dough

1. Cream together the butter and sugar in a large bowl. Once it is smooth and creamy, add in the vanilla.
2. In a separate bowl, whisk together the baking soda and buttermilk. Alternate adding the flour and the baking soda/buttermilk mixture to the creamed butter/sugar in three additions. Mix until combined, but do not overmix. Cover the bowl with plastic wrap and place in the refrigerator for at least an hour.
3. The next steps go pretty quickly so preheat the oven to 350 degrees Fahrenheit so that it is ready about 20 minutes from the time you remove the dough from the refrigerator. Line your baking sheets with parchment paper or a silicone baking mat.
4. Sprinkle flour on your work surface and rolling pin to avoid the dough from sticking to the table. Roll the dough into a rectangle that is approximately 12″x8″. It will be a bit thicker than 1/4″. I used my fingers as I was rolling it out to tuck the dough as needed to maintain a rectangular shape. Doing this allows the cookies to maintain a consistent size.
5. Use a butter knife to spread the softened butter onto the top of the dough. Mix the cinnamon and sugar together in a medium bowl, and sprinkle the mixture on top of the butter in an even layer. Spread as close to the edges as possible. It will look like a lot of mixture, but you will want to use it all.
6. Very gently, you will start rolling the dough inwards from the long side. I found it easiest to kind of push the edge of the dough up before rolling in from the outside base. I felt like this step really helped the dough to not crack and roll together easily.
7. Try to keep the roll as tight as you can, so that it doesn’t unroll when it is baking. If little cracks appear, just seal them up by pressing the dough back together.
8. Place the roll on a baking sheet and place in the refrigerator for another 15 minutes to firm up.
9. Remove the cookie roll from the baking sheet and slice into 1″ thick slices. I liked the 1″ thickness because it really made it look like a cinnamon roll more than a cookie. If you adjust the thickness, you may also need to adjust the time that it is baked.
10. Wipe the blade between each cut so that the cinnamon doesn’t spread, and help it look pretty out of the oven! I didn’t have problem with the dough sticking to the knife, but if you are struggling, feel free to spread a little flour on the knife to help it run through the dough easier.
11. Place the cookies onto the lined cookie sheet, allowing enough room for spreading. I placed 6 cookies on each pan. If any of the edges start to come undone, press them back into place. You can also use your hands to reshape the dough back into a round shape if it became irregular shaped.
12. Bake for 18-20 minutes until lightly browned. Allow the cookie to sit on the pan for a couple of minutes before transferring to a cooling rack. When you move the cookies, make sure your cookie spatula slides under the entire cookie. I had the outer spiral break off on a few because I didn’t reach all the way to the far end of the cookie. Allow the cookie to cool completely before applying the glaze.

How to Make The Icing Glaze

1. After the cookies are completely cooled, whisk together the confectioner’s sugar, vanilla and milk together in a small bowl until smooth. You will want to start with 3 tablespoons of milk and add more if you prefer a runnier texture.
2. If you are planning on drizzling it on top of the cookies you will want it runnier. I wanted it thicker because I dropped the frosting on top and I wanted to control how the glaze fell off with my spoon.