Cookie Box Mystery

This year's neighborhood Christmas cookie boxes were a mystery right up until bake day. Covid finally came to visit our family, four years into the pandemic and well... it hit me like a ton of bricks. I kept hemming and hawing about what cookies to make and finally decided I wanted to try these so these made the cut. These Cinnamon Roll Sugar Cookies are very fun. You make your own little cinnamon butter squares that get folded into the dough. They bake into these crispy cinnamon crunchies. I used a round cookie cutter to circle around the baked cookies to get them back into a round shape - something I've seen plenty but never felt the need to do. This made sense since some of the cinnamon butter crunchies ooze out a bit and make the cookie an odd shape and size.
These cookies were amazing. So good. Everyone in our house agreed these go on the make again list. I didn't ask the neighbors but I'm hoping they thought the same thing. Either way... we'll make them again. I was able to make the dough the night before then bake the next day - that worked out very well since I still had a kid in school but he didn't leave until 9 so I had cookies to bake before I went back to making magic for Christmas.

Cinnamon Roll Sugar Cookies
Ingredients
Cinnamon sugar filling:
4 tablespoons unsalted butter, softened
⅓ cup brown sugar, packed
1½ tablespoons all purpose flour
2½ teaspoons ground cinnamon
pinch salt
Cookies:
1 cup unsalted butter, softened but still cool to the touch
1 ⅓ cups granulated sugar
1 ¾ teaspoons pure vanilla extract
1 large egg
1 large egg yolk
2 ¾ cups all purpose flour,
¾ teaspoon baking powder
1 teaspoon cornstarch
¼ teaspoon salt

Preheat oven to 350°F with racks near the center. Line two baking sheets with parchment paper and set aside.
Cinnamon sugar filling:
Mix together all ingredients (I use a small rubber spatula or fork) until well combined. Place in the freezer for about 10 minutes while you prepare the cookie dough.
Cookies:
Using an hand mixer, or stand mixer fitted with the paddle attachment, beat butter and sugar until light and creamy. Add vanilla, egg, and egg yolk, and beat until combined, scraping the sides of the bowl as necessary.
In a separate bowl, combine flour (see note), baking powder, cornstarch, and salt. Slowly add the dry ingredients to the wet ingredients and beat until combined.
Remove half of the dough from the mixing bowl and spread the remaining dough out across the bottom the mixing bowl.
Remove the cinnamon mixture from the freezer and use two spoons to scoop small pieces (about a teaspoon each) of the cinnamon mixture and place them all over the dough in the mixing bowl.
Once you have used half of the cinnamon mixture, get the cookie dough that you have set aside, and spread it or press it with your fingers into a somewhat even layer on top of the cinnamon and dough in the mixing bowl.
Proceed to add the remaining cinnamon mixture (in little pieces) all over the top of that piece of dough. Your bowl should now have two layers of cookie dough, each layer topped with cinnamon sugar bits.
Step by step cinnamon roll cookie dough in a white bowl.
Once you have your dough layered you are going to fold and mix it just barely. I do two folds, scraping up and over, followed by one to two stirs by hand with a rubber spatula. Do not use an electric mixer, this needs to be a brief stir that leaves some pieces of the cinnamon mixture in chunks and some pieces swirled into the dough.
Cinnamon roll cookie dough in a white bowl with a rubber spatula.
Scoop the dough into two-tablespoon portions using a cookie scoop. Pay attention while scooping to ensure that each scoop has a fair amount of dough mixed with cinnamon.
Place the dough balls on a plate and freeze for 10 minutes. This quick chill firms up the butter so the cookies don't spread too much.
Scoops of cinnamon roll cookie dough on a white plate.
Place dough balls a couple inches apart on parchment lined baking sheets. For thicker cookies leave the dough balls in higher mounds, for thinner cookies give them a slight pat down before baking. Any dough balls that do not fit into this batch that's baking should be refrigerated (not frozen) until the baking sheets have cooled and you're ready to bake them.
Bake for 10-12 minutes, until the cookies have spread, the edges are beginning to brown and the center is still slightly underdone.
Some of the cookies will bake up a little misshapen. This is because pockets of cinnamon sugar might melt out while baking. Don't worry, I have two techniques that work for getting a perfectly round shape for every cookie in the batch! See notes for shaping cookies as soon as they come out of the oven.
Place baking sheets on wire racks and allow cookies to cool completely. They will firm up as they cool.