Preheat your oven to 350 degrees F and spray a 24-cup mini muffin tin with non-stick cooking spray.
Grab your chocolate chip cookie dough and slice it into 24 equal squares (just follow the perforated lines), then drop one square of cookie dough into each mini muffin tin cavity.
Bake for 12-15 minutes, then immediately take the handle of a spoon or spatula and press down in the center of each cookie to create a well and set aside to cool completely.
Once cooled, remove the cookie cups from the pan and place them on a baking sheet lined with parchment paper or a silicone baking mat. If the edges of the cookies seem to be stuck to the pan, run a butter knife around the edges to loosen each cup.
In a microwave safe bowl, combine the semi-sweet chocolate chips and vegetable oil. Microwave in 30 second intervals, stirring in between, until melted and smooth.
Dip the rim of each cookie cup into the melted chocolate, then return to the prepared baking sheet. Place them in the fridge for 15-20 minutes to set the chocolate.
In a medium mixing bowl, combine the ricotta cheese, mascarpone cheese, powdered sugar, and vanilla extract, then mix until smooth and creamy.
Transfer the cannoli filling into a piping bag or Ziploc bag optionally fitted with a piping tip, cut off the end, and generously fill each cookie cup.
Sprinkle mini chocolate chips on top of each one and dust with more powdered sugar before enjoying!