Whisk together flour, baking soda and salt in a medium-sized bowl. Set aside.
Cream butter and both sugars with an electric mixer until light and fluffy – approximately 2 to 3 minutes.
Add egg, egg yolk and vanilla then beat until incorporated. Scrape down the sides of the bowl with a spatula as needed.
Reduce mixer speed to low then add dry ingredients to wet, mixing until just combined.
Using a wooden spoon, gently stir in chocolate chips, finely ground Oreos and Oreos broken into small pieces until evenly distributed. Avoid overmixing.
Scoop cookie dough into balls using a large 2-tablespoon sized cookie scoop then place onto the parchment lined baking sheets, spacing cookies 2 inches apart.
Cover cookie sheets with plastic wrap then place in refrigerator to chill for 2 hours. Do not skip this step or cookies will be prone to spreading in the oven.
Preheat oven to 350 degrees. Line two large baking sheets with parchment paper then set aside.
Bake cookies for 11 - 13 minutes or until the edges are set but the centers are still soft. Avoid overbaking or cookies will be dry.
Remove cookies from oven then press the medium-sized Oreo pieces onto the tops of each.
Cool cookies on the baking sheet for 5 minutes then transfer to a baking rack to cool completely.
Store cookies in an airtight container at room temperature up to 3 days.