In a medium bowl, beat the softened cream cheese, powdered sugar, and vanilla extract until completely smooth and creamy with no lumps. Scoop into small portions (about 1 tablespoon each) and place onto a parchment-lined tray. Freeze for 20–30 minutes until firm.

In a large bowl, cream the softened butter, brown sugar, and granulated sugar together until light and fluffy, about 2–3 minutes. Add the eggs one at a time, mixing well after each addition, then mix in the vanilla extract until fully combined.

In a separate bowl, whisk together the flour, cocoa powder, baking soda, and salt until evenly combined. Gradually add the dry ingredients to the wet ingredients, mixing just until a thick dough forms. Do not overmix.

Gently fold the crushed Oreos into the dough until evenly distributed.

Scoop large portions of dough (about ¼ cup each for bakery-style cookies). Flatten each portion slightly, place a frozen cheesecake filling ball in the center, and carefully wrap the dough around it, sealing completely. Roll into tall dough balls for thick cookies.

Place assembled cookie dough balls in the refrigerator for 20–30 minutes to help prevent spreading.

Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper. Place cookies spaced apart and bake for 10–12 minutes, until the edges are set and the centers are slightly underbaked.

Allow cookies to cool on the baking sheet for at least 10–15 minutes before transferring. The centers will set as they cool, creating a creamy cheesecake interior.