In the bowl of a stand mixer fitted with the paddle attachment or in a large bowl if using a handheld mixer, cream the butter and sugars together on medium speed until light and fluffy, about 3 minutes. Add in the milk and vanilla. Turn the mixer to low and slowly add in the flour and salt. Turn the mixer off and fold in the chocolate chips. Set aside.

In a microwave-safe bowl, heat the chocolate chips and oil together in the microwave. Mix until everything is uniform.

Using a pastry brush, brush a layer of chocolate in your candy mold. Repeat with other molds. Place the molds in the freezer for about 10 minutes.

Remove the molds from the freezer and add a bit of cookie dough into the candy molds. Press down on it so the tops are flat (I found it helpful to shape the dough into a small ball and then putting them in the molds after that). Then using the pastry brush again, paint another layer of chocolate on top and enough to cover the cookie dough. Return the molds back to the freezer for another 10-15 minutes.

Unmold the candies and enjoy.