Cream the softened butter, brown sugar, and white sugar in a large bowl using a hand mixer or stand mixer with the paddle attachment. Start on low speed, then mix on medium for 8–10 minutes until light and fluffy, scraping the bowl once or twice.
Add the milk and vanilla and beat just until combined.
In a separate bowl, sift the flour, baking soda, and salt. Add this dry mixture to the creamed mixture and fold gently with a rubber spatula until a soft cookie dough forms. Do not overmix.
Fold in the chocolate chips evenly.
Weigh the dough and divide it into 8 equal portions (about 92 g each). Flatten each portion slightly, place an Oreo in the center, and wrap the dough fully around it. Seal the edges and roll into a smooth ball.
Place the stuffed dough balls on a parchment-lined baking sheet. Cover and chill for 4 hours or overnight.
When ready to bake, preheat the oven to 180°C (350°F). Arrange the chilled dough balls on a baking tray and bake for 13–15 minutes, until the edges are lightly golden and the centers still look soft.
While warm, press extra chocolate chips on top and sprinkle a tiny pinch of flaky sea salt.
Cool the cookies on the baking sheet for 8–10 minutes, then transfer to a cooling rack to finish cooling.
Notes
Double the recipe: The recipe can be easily doubled to make 12 cookies
Chilling is essential: It prevents overspreading and gives thick, soft cookies.
Weigh your dough: Keeping each ball around 92 g ensures even baking and proper Oreo coverage.
Fold, don’t beat: Overmixing leads to dense cookies.
Use softened, not melted butter: Melted butter causes excess spreading.
Underbake slightly: Cookies set as they cool, giving the perfect gooey center.
Cool on the tray: Helps them firm up without drying.
For prettier cookies: Add extra chocolate on top and swirl with a cookie cutter for round edges.
Freezing: Stuffed dough balls freeze well. Bake from frozen with 2–3 minutes extra.