In a large mixing bowl or stand mixer fitted with the paddle attachment, beat the softened butter, light brown sugar, and granulated sugar together on medium speed for 2–3 minutes, until light and fluffy. If the butter looks lumpy, let the mixture sit 5–10 minutes, then beat again.
1 cup unsalted butter, 1 cup light brown sugar, 1/2 cup granulated sugar
Add the eggs one at a time, mixing just until each egg is incorporated. Scrape down the sides of the bowl as needed. Mix in the vanilla extract until the batter looks creamy and smooth.
2 large eggs, 2 teaspoons pure vanilla extract
In a separate bowl, whisk together the all-purpose flour, baking soda, baking powder, and fine sea salt until well combined.
3 cups all-purpose flour, 1 teaspoon baking soda, 1/2 teaspoon baking powder, 1 teaspoon fine sea salt
Add the dry ingredients to the butter mixture in two additions, mixing on low speed just until no streaks of flour remain. Do not over-mix to keep the cookies chewy.
Fold in the semi-sweet chocolate chips with a spatula or on the lowest mixer speed. If using, gently fold in the crushed Oreo cookies to distribute them evenly through the dough.
1 1/2 cups semi-sweet chocolate chips, 1/2 cup crushed Oreo cookies
Cover the bowl and chill the dough in the refrigerator for at least 30–45 minutes and up to 24 hours. Chilled dough spreads less and bakes into thicker, softer cookies.
Line two large baking sheets with parchment paper or silicone baking mats. Count out 24 Oreo cookies for stuffing and set aside.
24 Oreo cookies
Preheat the oven to 350°F (175°C). Allow at least 15 minutes for the oven to come fully to temperature.
Scoop about 2 heaping tablespoons of chilled dough (around 2 oz / 55–60 g) for each cookie. Flatten the dough slightly in your hand, place an Oreo in the center, and wrap the dough around it, sealing all edges so no Oreo shows. Roll gently into a ball and place on the prepared baking sheet, spacing cookies 2–3 inches apart.
3 cups all-purpose flour, 1 1/2 cups semi-sweet chocolate chips, 24 Oreo cookies
If desired, press a few extra chocolate chips, mini chocolate chips, or sprinkles into the tops of each dough ball. Lightly sprinkle with flaky sea salt for a sweet-salty finish, if using.
flaky sea salt, mini chocolate chips or sprinkles
Bake one sheet at a time on the center rack for 11–14 minutes, until the edges are set and lightly golden and the centers still look slightly soft and puffed. The cookies will continue to cook on the hot pan after you remove them from the oven.
Let the cookies cool on the baking sheet for about 10 minutes to firm up around the Oreo center. Carefully transfer to a wire rack to cool completely, or enjoy warm for a gooey center.