Position a rack in the center of the oven and preheat the oven to 350°F. Line two baking sheets with parchment paper.
In a large bowl, use an electric mixer to cream the room-temperature butter with the packed light brown sugar and granulated sugar until fully combined and smooth, about 3 minutes. Scrape down the bowl as needed.
Add the egg and egg yolk, then add the ground cinnamon, vanilla extract, baking soda, and salt. Beat until the mixture is completely smooth, about 1 minute, scraping the bowl once if needed.
Using a wooden spoon or spatula, stir in the all-purpose flour and rolled oats until no streaks of flour remain and the dough is evenly mixed.
Fold in the chopped dark chocolate until evenly distributed through the dough.
Using a medium cookie scoop (about 1 1/2 tablespoons), portion the dough onto the prepared baking sheets, placing the scoops at least 2 inches apart.
Bake the cookies in the preheated oven until the edges are golden brown and the cookies are firm around the edges, 9 to 11 minutes.
Remove the baking sheet from the oven and let the cookies cool on the baking sheet for about 5 minutes, then transfer the cookies to a wire rack to cool completely before serving.