Make the cheesecake filling: In a small bowl, mix together the softened cream cheese, granulated sugar, and vanilla until smooth.

Scoop the cheesecake filling into 6 individual 1-tablespoon dollops onto a parchment-lined plate or baking sheet. Freeze until firm.

Make the cookie dough: In a medium bowl, mix together the softened butter, brown sugar, and granulated sugar.

Add the egg yolk and vanilla extract and mix until combined.

Add the flour, baking soda, baking powder, and salt. Mix until a dough begins to form.

The dough may seem crumbly. Use your hands to press and knead it together until it forms a cohesive dough.

Mix in the crushed Oreos and optional chocolate chips.

Divide the dough into 6 equal portions. Each cookie should be about 50-60 grams.

Flatten one portion into a thick disc and place one frozen cheesecake filling dollop in the center.

Bring the edges of the dough around the filling and pinch tightly to completely seal it inside. Repeat with the remaining cookies.

Place the stuffed cookies in the refrigerator for 30 minutes.

While the cookies chill, preheat the oven to 350°F.

Arrange the chilled cookies on a parchment-lined baking sheet with space between each one.

Bake for 11–13 minutes, until the edges are set and lightly golden.

Allow the cookies to cool completely.

Make the glaze: Whisk together the powdered sugar and 1 teaspoon of milk. Add additional milk a few drops at a time until the glaze reaches a thick, drizzleable consistency.

If desired, stir very finely crushed Oreos into the glaze.

Drizzle the glaze over the cooled cookies, allow it to set, and enjoy!