Preheat the oven to 350°F (180°C). Line two baking sheets with parchment paper and set aside. If you prefer firmer shaping, place one sheet in the fridge to chill while you portion dough.
In a medium bowl whisk together the flour, baking soda, and salt until evenly combined. Set this dry mix aside.
In the bowl of a stand mixer (or using a large bowl and a hand mixer), cream the softened butter with the brown and granulated sugars on medium-high for 3–4 minutes until the mixture is pale and fluffy. Scrape the bowl.
Beat in the vanilla, egg, and extra egg yolk until smooth and glossy, about 30–45 seconds. Sprinkle in the espresso powder and mix briefly just to incorporate.
With the mixer on low, add the dry flour mixture in two additions, mixing just until no streaks of flour remain. Avoid overmixing to keep the cookies tender.
Fold in the chocolate chips, the 1/2 cup of finely crushed Oreo crumbs, and most of the Oreo chunks by hand until evenly distributed, reserving a handful of chunks and some crumbs for topping.
Portion the dough using a large cookie scoop (about 3 oz / heaping scoop). Place scoops 2 inches apart on the prepared baking sheets. For more uniform cookies, chill the scooped dough on the sheet in the refrigerator for 30–45 minutes (or freeze for 10 minutes) so they spread less in the oven.
Before baking, gently press a few reserved Oreo pieces and extra chocolate chips onto the top of each dough ball for an attractive finish.
Bake one sheet at a time in the center of the oven for 11–13 minutes, until the edges are set and starting to turn golden but the centers still look slightly soft. If baking two sheets, swap their positions halfway through the bake.
Remove the cookies from the oven and let them cool on the baking sheet for 4–5 minutes. Use a spatula or the rounded edge of a glass to gently nudge and round any misshapen cookies while still warm, then transfer to a wire rack to cool completely.
Once cooled to warm or room temperature, sprinkle a few extra Oreo crumbs on top if desired. Store cooled cookies in an airtight container at room temperature for up to 4 days, or freeze for longer storage.