In a medium bowl, whisk together the flour, black cocoa powder, baking soda, and salt. Set this bowl aside while you work on the wet ingredients. Whisking first keeps the cocoa powder from clumping later, so the batter mixes up smooth.
Beat the softened butter on medium speed for about 2-3 minutes until it turns pale and fluffy. Add both sugars and continue beating for another 2 minutes, scraping down the bowl as needed. This step builds air into the dough, which keeps your cookies soft in the middle.
Mix in the eggs one at a time, then add the vanilla extract. Beat just until everything is fully combined and glossy. Don't overmix here, or the cookies can turn out tougher instead of tender.
Slowly add the dry flour mixture into the butter mixture on low speed. Mix only until you no longer see streaks of flour, since overworking the dough makes chewy cookies turn dense. The dough will look thick, dark, and slightly sticky.
Using a spatula, gently fold in the chopped Halloween Oreos and chocolate chips if using. Try to keep some larger Oreo chunks intact so you get that classic cookies-and-cream bite in every mouthful. Save a few extra pieces to press on top later.
Cover the bowl and refrigerate the dough for at least 30 minutes. Chilling firms up the butter so your cookies bake thick instead of spreading thin. If you're short on time, 15 minutes in the freezer works too.
Preheat your oven to 350°F and line a baking sheet with parchment paper. Scoop 2-tablespoon balls of dough, space them a few inches apart, and press a reserved Oreo piece on top of each. Bake for 10-12 minutes until the edges look just set.
Let the cookies rest on the hot baking sheet for 5 minutes before moving them to a wire rack. They'll continue cooking slightly from residual heat, so don't skip this resting step. Once fully cool, they're ready to serve or decorate.